Acetic Acid → 2-(Methoxymethyl)-4-thiazolecarboxaldehyde

HRID 1174128Notes

Reaction equation

HRID 1174128 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](OCC)=[O:10])[N:8]=1.CC(C[AlH]CC(C)C)C.C(O)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 45117589HCID 45117589, compound

Product 1

HCID 451217662-(Methoxymethyl)-4-thiazolecarboxaldehydeYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution containing the product from Example 6C (7.4 g, 36.8 mmol) in dichloromethane (40 mL) was treated with DIBAL (73.6 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) at −78° C. and warmed to 25° C. A 10% solution of aqueous sodium potassium tartrate was added and the mixture was stirred vigorously for 1 hour. The reaction mixture was partitioned between chloroform and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (5.78 g, 71% yield).

Workup

  1. temperaturewarmed to 25° C
  2. stirringthe mixture was stirred vigorously for 1 hour
  3. customThe reaction mixture was partitioned between chloroform 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 with 0-100% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-c757adf5ec8845cbb1f882e44d411b16
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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