Acetic Acid → 2-Isopropylthiazole-4-carbaldehyde

HRID 1174274Notes

Reaction equation

HRID 1174274 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].CC(C[AlH]CC(C)C)C.C(O)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 10535999Ethyl 2-isopropylthiazole-4-carboxylate

Product 1

HCID 27631922-Isopropylthiazole-4-carbaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution containing the product from Example 56B (18 g, 90.5 mmol) in dichloromethane (100 mL) was treated with DIBAL (150 mL, 1 M in dichloromethane) dropwise at −78° C. over 2 hours, stirred at −78° C. for 2 hours, treated with acetic acid (10 mL), warmed to 25° C., treated with 10% solution of aqueous sodium potassium tartrate, stirred vigorously for 1 hour, and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting 0-5% ethyl acetate in dichloromethane to give the title compound (5.24 g, 40% yield).

Workup

  1. temperaturewarmed to 25° C.
  2. stirringstirred vigorously for 1 hour
  3. custompartitioned between dichloromethane and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting 0-5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-34bbb629f01f4851b209fc28f07dd8d8
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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