Isopropyltriphenylphosphonium iodide → (+/-)-n-Butyl-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]-formate

HRID 1590386Notes

Reaction equation

HRID 1590386 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)[CH3:2].[I-].[CH:19]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:21])[CH3:20].[CH2:41]([Li])[CH2:42]CC>O1CCCC1>[CH2:1]([O:3][C:4]([C@H:5]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:15])([F:16])[F:14])[CH:8]=2)[C:19]1([CH3:21])[CH3:20])=[O:17])[CH2:2][CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 53394832Ethyl 3-[3-(trifluoromethyl)phenyl]prop-2-enoateHCID 178418339Butyllithium

Product 1

HCID 86746725(+/-)-n-Butyl-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]-formate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-3-trifluoromethylcinnamate (0.98 g) (Example 2) in tetrahydrofuran under nitrogen was treated with the ylid prepared from isopropyl triphenylphosphonium iodide (2.12 g) and n-butyllithium (2.8 ml). After 20 hours at 80° the mixture was worked up in the usual manner. Purification by chromatography (silica; ether/hexane) gave (±)-n-butyl-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]-formate (0.78 g). NMR 1H: 7.22(4H,m), 4.20(2H,m), 2.72(1H,m), 2.00(1H,m), 1.40(7H,m), 0.89(6H,m).

Workup

  1. customPurification by chromatography (silica; ether/hexane)

Sources & evidence

ORD record
ord-6d811203af0c4bcf8c01a2175abdeb26
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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