Water → 4-Isopropyl-1,3-thiazole-2-carbaldehyde

HRID 23441Notes

Reaction equation

HRID 23441 reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=1)=O)C.CC(C[AlH]CC(C)C)C.O>C(Cl)Cl>[CH:11]([C:9]1[N:10]=[C:6]([CH:4]=[O:3])[S:7][CH:8]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydride2×HCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Product 1

HCID 110841104-Isopropyl-1,3-thiazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.1 g (11 mmol) of 4-isopropyl-thiazole-2-carboxylic acid ethyl ester (J. Med. Chem., 1998:602-617) in CH2Cl2 (50 mL) was cooled to −78° C. under nitrogen and treated dropwise with DIBAL (12 mL of 1.0 M in CH2Cl2; 12 mmol). The mixture was stirred at low temperature for 1 hour and then treated with another 7 mL of DIBAL. The solution was stirred for 30 minutes at −78° C. H2O was added, and the mixture was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated. Chromatography of the residue over silica gel, eluting with 3:1 hexane:EtOAc, gave the title compound.

Workup

  1. stirringThe solution was stirred for 30 minutes at −78° C
  2. extractionthe mixture was extracted with EtOAc (3×100 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 3:1 hexane

Sources & evidence

ORD record
ord-f1e029d76a9847eeb11dbe8a09e7637d
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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