Ammonium Chloride → (4-Phenylthiophen-2-yl)methanol

HRID 2286190Notes

Reaction equation

HRID 2286190 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[O:13])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12][OH:13])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 50094674-Phenylthiophene-2-carbaldehyde

Product 1

HCID 12941349(4-Phenylthiophen-2-yl)methanolYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 4-phenyl-2-thiophenecarboxaldehyde (4.32 g) in absolute ethanol (85 ml) was cooled in an ice-bath and treated with NaBH4 (1.06 g). After 20 min. the mixture was allowed to attain ambient temperature when stirring was continued for 6h. Saturated aqueous NH4Cl (30 ml) was then carefully added to the vigorously stirred mixture, and the resulting suspension extracted with ER (2×200 ml). The combined extracts were dried (Na2SO4 /K2CO3), filtered and evaporated to give the title compound (4.2 g) as crystals, m.p. 112°-113°.

Workup

  1. temperaturewas cooled in an ice-bath
  2. customto attain ambient temperature
  3. waitwas continued for 6h
  4. extractionthe resulting suspension extracted with ER (2×200 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4 /K2CO3)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f46f420f079f4a459b52e7d8a6d35d06
Source dataset
uspto-grants-1982_04
Patent number
US04327092

Reaction notes

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