Citation: Huan Luo, Yan-Fei Liu, Chun-Lei Zhang, Yan Wang, Gang Ni, De-Quan Yu. A new method for the synthesis of 3-hydroxymethylbenzofuran[J]. Chinese Chemical Letters, ;2013, 24(12): 1115-1117. shu

A new method for the synthesis of 3-hydroxymethylbenzofuran

1.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Corresponding author: De-Quan Yu,
Received Date: 13 May 2013
Available Online: 14 June 2013
Fund Project: The project was supported by the National Mega-Project for Innovative Drugs (No. 2012zx09301002-002) (No. 2012zx09301002-002)

A new one-step synthesis of 3-hydroxymethylbenzofuran, based on intramolecular cyclization of 2- (methoxymethyl)-2-(2'-methoxymethyl-4'-methylphenyl)-butanone 1 under diluted hydrochloric acid in THF, was developed. The mechanism for this process was investigated via chemical equilibrium shift of tautomer in acidic conditions. The applicability of this new method was studied further in this paper.
- 3-Hydroxymethylbenzofuran derivatives,
- Mechanism,
- Tautomer
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  [11] Analytical data for compound: 3a: ¹H NMR (300 MHz, CDCl₃): δ 7.58 (m, 1H), 7.39 (m, 1H), 7.23 (m, 2H), 4.74 (s, 2H), 2.45 (s, 3H); ¹³C NMR (75 MHz, CDCl₃): δ 154.2, 153.0, 128.6, 123.8, 122.8, 119.2, 114.4, 110.9, 55.7, 12.3; HR-ESI-MS: calcd. for C₁₀H₁₀NaO₂⁺: 185.0573; found: 185.0579 [M+Na]⁺. 3b: ¹H NMR (300 MHz, CDCl₃): δ 7.40 (d, 1H, J = 7.8 Hz), 6.16 (s, 1H), 7.00 (d, 1H, J = 7.8 Hz), 4.64 (s, 2H), 2.42 (s, 3H), 2.37 (s, 3H); ¹³C NMR (75 MHz, CDCl₃): δ 154.5, 152.2, 133.8, 126.1, 124.0, 118.6, 114.2, 111.1, 55.5, 21.7, 12.1; HR-ESI-MS: calcd. for C₁₁H₁₂NaO₂⁺: 199.0730; found 199.0735 [M+Na]⁺. 3c: ¹H NMR (300 MHz, CDCl₃): δ 7.51 (d, 1H, J = 7.8 Hz), 7.42 (s, 1H), 7.293 (d, 1H, J = 7.8 Hz), 4.73 (s, 2H), 2.43 (s, 3H), 1.36 s (s, 9H); ¹³C NMR (75 MHz, CDCl₃): δ 154.6, 152.6, 147.8, 125.9, 120.5, 118.5, 114.2, 107.7, 55.8, 35.1, 31.9, 12.3; HR-ESI-MS: calcd. for C₁₄H₁₈NaO₂⁺: 241.1199; found 241.1203 [M+Na]⁺.
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  [13] 1HNMRdata for compound: 4: 1HNMR(300 MHz, CDCl₃): δ 7.82 (brs, 1H), 7.16 (s, 1H), 6.75 (s, 1H), 6.61 (s, 1H), 2.30 (s, 3H), 2.05 (s, 3H), 1.72 (s, 3H). 5: ¹H NMR (300 MHz, CDCl₃): δ 7.19 (s, 1H), 6.75 (s, 1H), 6.69 (s, 1H), 2.30 (s, 3H), 1.54 (s, 3H), 1.51 (s, 3H).
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沈阳化工大学材料科学与工程学院沈阳 110142