Sodium borohydride → HCID 14931752, compound

HRID 1252064Notes

Reaction equation

HRID 1252064 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[O:13])[N:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(OC(C)C)(C)C>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][OH:13])[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14931751HCID 14931751, compound

Product 1

HCID 14931752HCID 14931752, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 2-acetylamino-4-(2-formylethyl)thiazole (2.49 g) in diisopropyl ether (170 ml) was added sodium borohydride (120 mg) under ice-cooling and stirred for 1 hour at the same temperature. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V) to give 2-acetylamino-4-(3-hydroxypropyl)thiazole (1.70 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V)

Sources & evidence

ORD record
ord-8c1d5bc708904421b98091bce04cbefd
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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