Hydrochloric Acid → 4-Dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one
Reaction equation
[BH4-].[Na+].O[CH:4]([C@H:9]1[C:11]([CH3:13])([CH3:12])[C@H:10]1[C:14]([OH:16])=[O:15])[C:5]([Cl:8])([Cl:7])Cl.Cl>CN(C)C=O.O>[Cl:8][CH:5]([Cl:7])[CH:4]1[CH:9]2[CH:10]([C:11]2([CH3:12])[CH3:13])[C:14](=[O:15])[O:16]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Sodium borohydride (0.12 mmol) was added to a solution of cis 2-(1-hydroxy-2,2,2-trichloroethyl)-3,3-dimethylcyclopropane carboxylic acid (0.12 mol) in dry dimethylformamide (0.4 ml), and the mixture was heated for 30 minutes at 80° C. An additional amount of 0.12 mmol sodium borohydride was then added and the mixture was heated for a further 15 minutes at 80° C. It was then diluted with water, acidified with concentrated HCl and extracted with deuterochloroform, CDCl3. The extract was washed with water and analysed by NMR, which showed a yield of 25% of the desired product, with 30% of unconverted starting material.
Workup
- temperaturethe mixture was heated for a further 15 minutes at 80° C
- extractionextracted with deuterochloroform, CDCl3
- washThe extract was washed with water and analysed by NMR, which
Sources & evidence
- ORD record
- ord-1172febbe3854caaae15a576756d9404
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04346038
Reaction notes
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