Ammonium Chloride → 4-Ethyl-2-thiophenemethanol

HRID 1828435Notes

Reaction equation

HRID 1828435 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[O:9])[S:6][CH:7]=1)[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 152096224-Ethylthiophene-2-carbaldehyde

Product 1

HCID 232612874-Ethyl-2-thiophenemethanolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Ethyl-2-thiophenecarbaldehyde (1 g, 7.13 mmol) dissolved in methanol (7 ml) was added with sodium borohydride (135 mg, 3.57 mmol) under ice cooling, stirred for 10 minutes and then further added with sodium borohydride (150 mg, 3.96 mmol) at 0° C. After the reaction solution was stirred under ice cooling for 30 minutes, the reaction was stopped with saturated aqueous ammonium chloride and the reaction solution was extracted with chloroform. The organic layer collected was dried over magnesium sulfate and concentrated under reduced pressure to obtain 1 g (100%) of the title compound without purification.

Workup

  1. stirringAfter the reaction solution was stirred under ice cooling for 30 minutes
  2. extractionthe reaction solution was extracted with chloroform
  3. customThe organic layer collected
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ccaa916835af4b6f91c4d27618e9e2b7
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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