Ethanol → (4-Isopropylthiazol-2-yl)methanol

HRID 1609321Notes

Reaction equation

HRID 1609321 reaction equation
[C:1]([C:6]1[S:7][CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=1)(OCC)=[O:2].C(O)C.[BH4-].[Na+]>O>[CH3:12][CH:11]([C:9]1[N:10]=[C:6]([CH2:1][OH:2])[S:7][CH:8]=1)[CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Product 1

HCID 10678505(4-Isopropylthiazol-2-yl)methanolYield 112.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.5 g of 2-carboethoxy-4-(1-methylethyl)thiazole, 100 ml of ethyl alcohol and 1.1 g of sodium borohydride was heated to reflux for 4 hr. The reaction mixture was then condensed to one half of the original volume in vacuo, diluted with 150 ml of water and extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4) and condensed in vacuo to give 4.0 g of 4-(1-methylethyl)-2-thiazole methanol; m.p. 80°-82° C.

Workup

  1. temperatureto reflux for 4 hr
  2. customcondensed to one half of the original volume in vacuo
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. customdried
  6. custom(MgSO4) and condensed in vacuo

Sources & evidence

ORD record
ord-aacb3b9912d1441fa4b2e07b984c824c
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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