Sodium borohydride → 2-Cyclobutyl-4-thiazole methanol

HRID 327569

Reaction equation

HRID 327569 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[N:9]=[C:10]([CH:13]2[CH2:16][CH2:15][CH2:14]2)[S:11][CH:12]=1)=O)C>C(O)C>[CH:13]1([C:10]2[S:11][CH:12]=[C:8]([CH2:6][OH:5])[N:9]=2)[CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54513950Ethyl 2-cyclobutylthiazole-4-carboxylate

Product 1

HCID 539708732-Cyclobutyl-4-thiazole methanolYield 101.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.3 g) was added in portions over a 10 min period to an ice cold solution of 6.3 g of 2-cyclobutyl-4-thiazolecarboxylic acid ethyl ester in 100 ml of ethyl alcohol. The ice bath was removed and the reaction mixture stirred at room temperature for 30 hr during which an additional 0.46 g of sodium borohydride was added. The reaction mixture was then diluted with 200 ml of ice water and extracted with ethyl ether. The combined extracts were washed with water, dried (MgSO4) and condensed in vacuo to yield 5.1 g of 2-cyclobutyl-4-thiazole methanol as an oil.

Workup

  1. customThe ice bath was removed
  2. additionwas added
  3. additionThe reaction mixture was then diluted with 200 ml of ice water
  4. extractionextracted with ethyl ether
  5. washThe combined extracts were washed with water
  6. customdried
  7. custom(MgSO4) and condensed in vacuo

Sources & evidence

ORD record
ord-a162371cebec4ca8b6fc1fcf978e3bbe
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Linked notes

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