tert-Butanol → Tert-butyl 3-cyclopropyl-3-oxopropanoate
Reaction equation
[CH:1]1([C:4]([CH:6]2[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])OC2=O)=[O:5])[CH2:3][CH2:2]1.[C:16](O)(C)(C)C>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:5])[CH2:6][C:11]([O:10][C:9]([CH3:13])([CH3:14])[CH3:16])=[O:12])[CH2:2][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 5-cyclopropylcarbonyl-2,2-dimethyl-1,3-dioxan-4,6-dione (23.9 g) and t-butanol (25 g) in dry toluene (80 ml) was stirred and heated at 80° C. for 4 hours. The cooled mixture was washed with water (3×30 ml), dried (anhydrous sodium sulphate), treated with decolourizing charcoal and filtered. The filtrate was evaporated to dryness and the residue was distilled to give t-butyl 3-cyclopropyl-3-oxopropionate (20.2 g) as a clear oil bp 80°-84° C./8 mmHg.
Workup
- washThe cooled mixture was washed with water (3×30 ml)
- dry with materialdried (anhydrous sodium sulphate)
- additiontreated with decolourizing charcoal
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-9ca52d129f2f49fe882326312898a225
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05747424
Reaction notes
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