Acetic Acid → 4-(Hydroxymethyl)-2-Isopropylthiazole
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.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]([CH2:9][OH:10])[N:8]=1)([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution containing the product from Example 56B (18 g, 90.5mmol) in dichloromethane (100 mL) was treated with diisobutyl aluminum hydride (150 mL, 1 M in dichloromethane) dropwise at −78° C. over 2 hours and the mixture was stirred at −78° C. for 2 hours. Acetic acid (10 mL) was added at −78° C. and the mixture was 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 was partitioned between dichloromethane and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-5% ethyl acetate/dichloromethane to give the title compound (3.84 g, 27% yield).
Workup
- temperaturethe mixture was warmed to 25° C
- stirringthe mixture was stirred vigorously for 1 hour
- customThe reaction was partitioned between dichloromethane and water
- washthe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was chromatographed on silica gel eluting with 0-5% ethyl acetate/dichloromethane
Sources & evidence
- ORD record
- ord-bccd9c44618b407f8d089e5d49f6bfd4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834043B2
Reaction notes
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