Ethanol → (3-(5-Methyl-thiophen-2-ylmethyl)-phenyl)-methanol

HRID 1927274Notes

Reaction equation

HRID 1927274 reaction equation
C(O)C.[CH3:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=[O:15])=[CH:7][CH:6]=1.[BH4-].[Na+]>O>[CH3:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:12]=[C:13]([CH2:14][OH:15])[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 592873823-(5-Methyl-thiophen-2-ylmethyl)-benzaldehyde

Product 1

HCID 59287391(3-(5-Methyl-thiophen-2-ylmethyl)-phenyl)-methanolYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethanol (5.0 mL) and 3-(5-methyl-thiophen-2-ylmethyl)-benzaldehyde (350 mg) described in Manufacturing Example 52-2 was added sodium borohydride (120 mg), which was stirred for 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (300 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe solvent was evaporated from the organic layer under a reduced pressure
  3. customthe residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6b304798ff4a446cace12547705eb42e
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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