Water → 5-Isopropylthiazole-4-carbaldehyde

HRID 23440Notes

Reaction equation

HRID 23440 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][S:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.CC(C[AlH]CC(C)C)C.O>C(Cl)Cl>[CH:10]([C:9]1[S:8][CH:7]=[N:6][C:5]=1[CH:3]=[O:2])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydride2×HCID 13015587Methyl 5-isopropylthiazole-4-carboxylate

Product 1

HCID 111373865-Isopropylthiazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.8 g (37 mmol) of 5-isopropyl-thiazole-4-carboxylic acid methyl ester (J. Chem. Soc., Perkin Trans. 1, 1982:159-164) in CH2Cl2 (120 mL) was cooled to −78° C. under nitrogen and treated dropwise with DIBAL (37 mL of 1.0 M in CH2Cl2; 37 mmol). The mixture was stirred at low temperature for 45 minutes and then treated with another 20 mL of DIBAL. The solution was stirred for 1 hour at −78° C. H2O was added, and the mixture was extracted with EtOAc (3×150 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated. Chromatography of the residue over silica gel, eluting with 2:1 hexane:EtOAc, gave the title compound.

Workup

  1. stirringThe solution was stirred for 1 hour at −78° C
  2. extractionthe mixture was extracted with EtOAc (3×150 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washChromatography of the residue over silica gel, eluting with 2:1 hexane

Sources & evidence

ORD record
ord-530d04ee3212479b9a176b43e26151ce
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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