2-Benzofurancarboxaldehyde, 5-methoxy- → (5-Methoxy-1-benzofuran-2-yl)methanol

HRID 2061354Notes

Reaction equation

HRID 2061354 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]=[O:12])=[CH:8][C:7]=2[CH:13]=1.[BH4-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][OH:12])=[CH:8][C:7]=2[CH:13]=1

Participants

4

Reactant 2

HCID 316632-Benzofurancarboxaldehyde, 5-methoxy-HCID 4311764Sodium borohydride

Product 1

HCID 15161064(5-Methoxy-1-benzofuran-2-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound 24 (3.5 g, 19.9 mmol) was dissolved in EtOH (20 mL). NaBH4 (957 mg, 25.87 mmol) was added portionwise at 0° C., with vigorous stirring. The suspension was stirred at 0° C. for 15 min and then at room temperature for 1.5 h. Solvent was evaporated off in-vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (2:1) to give 25 (3.0 g, 85%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 7.36 (1H, d, J=8.90 Hz, H-7), 7.02 (1H, d, J=2.6, H-4), 6.90 (1H, dd, J=6.30 & 2.60, H-6), 6.61 (1H, s, H-3), 4.76 (2H, s, 2-CH2), 3.86 (3H, s, OCH3), 2.16 (1H, bs, OH). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 113.07 (C-7), 111.69 (C-6), 104.34 (C-4), 103.60 (C-3), 58.24 (CH2), 55.92 (OCH3).

Workup

  1. waitat room temperature for 1.5 h
  2. customSolvent was evaporated off in-vacuo
  3. custompurified by flash chromatography
  4. washeluting with hexane/EtOAc (2:1)

Sources & evidence

ORD record
ord-0e53f03e2c704296b92e0ec8f5aaa247
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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