Ethyl 2-isopropylthiazole-4-carboxylate → 2-Isopropylthiazole-4-carbaldehyde

HRID 433762Notes

Reaction equation

HRID 433762 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9](OCC)=[O:10])[N:8]=1)([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10535999Ethyl 2-isopropylthiazole-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27631922-Isopropylthiazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-isopropylthiazole-4-carboxylate (1 mmol) in 50 ml of dry dichloromethane was cooled to −78° C. under N2 atmosphere and treated dropwise with 1.2 mmol of diisobutylaluminum hydride (1.5 M in toluene). The resulting solution was stirred for 0.5 h, quenched with aqueous Rochelle salts, extracted with dichloromethane, dried over Na2SO4, and concentrated in vacuo to provide the crude desired compound.

Workup

  1. customquenched with aqueous Rochelle salts
  2. extractionextracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-829c710b91074cdea58690f5e9d54825
Source dataset
uspto-grants-2003_12
Patent number
US06667404B2

Reaction notes

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