Water → HCID 10909824, compound

HRID 23438Notes

Reaction equation

HRID 23438 reaction equation
C([O:3][C:4]([C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH:11]([CH3:13])[CH3:12])=O)C.CC(C[AlH]CC(C)C)C.O>C1(C)C=CC=CC=1>[OH:3][CH2:4][C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 13015600Ethyl 4-isopropylthiazole-5-carboxylate

Product 1

HCID 10909824HCID 10909824, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.9 g (30 mmol) of 4-isopropyl-thiazole-5-carboxylic acid ethyl ester (J. Chem. Soc., Perkin Trans. 1, 1982:159-164) in toluene (100 mL) was cooled in an ice bath under nitrogen and treated dropwise with DIBAL (150 mL of 1.0 M; 150 mmol). The mixture was stirred at low temperature for 45 minutes and then allowed to warm to room temperature overnight. H2O was added cautiously, and the mixture was extracted with EtOAc (3×200 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated. The crude 5-(hydroxymethyl)-4-isopropyl-thiazole thus obtained was used as is in the next step.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×200 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf2171462fe843d896eccc484155b9db
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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