Sodium borohydride → 2-Cyclobutyl-4-thiazole methanol

HRID 1609331

Reaction equation

HRID 1609331 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-b6e6e4147fd74d2584f307bd85b9e15a
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Linked notes

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