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

HRID 1081150Notes

Reaction equation

HRID 1081150 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 (1.5M 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-3b71868e77214fbda82039760c95a466
Source dataset
uspto-grants-1996_12
Patent number
US05583232

Reaction notes

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