4,6,6-Trichloro-7,7,7-trifluoro-3,3-dimethylheptanoic acid → Methyl 3-(2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethyl-cyclopropane carboxylate
Reaction equation
Cl[CH:2]([CH2:10][C:11]([Cl:17])([Cl:16])[C:12]([F:15])([F:14])[F:13])[C:3]([CH3:9])([CH3:8])[CH2:4][C:5]([OH:7])=[O:6].[CH3:18]C(C)([O-])C.[Na+]>C(O)(C)(C)C.CN(C=O)C>[Cl:16][C:11]([Cl:17])([C:12]([F:15])([F:14])[F:13])[CH2:10][CH:2]1[CH:4]([C:5]([O:7][CH3:18])=[O:6])[C:3]1([CH3:9])[CH3:8]Participants
4
Procedure
The (−) enantiomer of the methyl ester of 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoic acid (14.43 gm) was cyclised with sodium t-butoxide base (6.3 gm 100%) in t-butanol/DMF solvent at <0° C. to produce methyl 3-(2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethyl-cyclopropane carboxylate which was isolated by quenching with water and extracting into dichloromethane. After washing with water and brine the product was obtained as a yellow/orange oil (10.1 gm) by topping off the dichloromethane solvent. The product obtained was analysed by GLC, GCMS and NMR to confirm the material was consistent with that of methyl 3-(2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethyl-cyclopropane carboxylate and it had a 80/20 cis:trans ratio.
Sources & evidence
- ORD record
- ord-eec7047873f048b2827c100e46c30a3f
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875885B2
Reaction notes
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