Diethyl Ether → 2-Benzofuran-3-yl-ethanol

HRID 502503Notes

Reaction equation

HRID 502503 reaction equation
CO[C:3](=O)[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1.[Li].CC[O:18]CC>>[CH:6]1[O:7][C:8]([CH:13]([OH:18])[CH3:12])=[C:9]2[CH:10]=[CH:11][CH:3]=[CH:4][C:5]=12

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 3028194LithiumHCID 10976279Methyl Benzofuran-3-acetate

Product 1

HCID 684582562-Benzofuran-3-yl-ethanol

Procedure

A solution of benzofuran-3-yl-acetic acid methyl ester (4.0 g, 21 mmol) in 25 ml of ether was added dropwise at RT to a suspension of lithium alanate (1.61 g, 59.5 mmol) in 35 ml of ether, and stirring was then carried out for 30 minutes. Excess alanate was then hydrolysed with ethanol, the mixture was suction-filtered over Kieselguhr, and the solvent was removed in vacuo. The product was obtained in the form of a yellowish oil in a yield of 3.0 g (89%).

Workup

  1. filtrationhydrolysed with ethanol, the mixture was suction-filtered over Kieselguhr
  2. customthe solvent was removed in vacuo
  3. customThe product was obtained in the form of a yellowish oil in a yield of 3.0 g (89%)

Sources & evidence

ORD record
ord-59bad4e82581494b96c626227b667a12
Source dataset
uspto-grants-2010_08
Patent number
US07776848B2

Reaction notes

Loading…