Hydrochloric Acid → (+/-)-[trans-3-(3-Trifluoromethylphenyl)-2,2-dimethylcyclopropyl]methanol

HRID 1590387Notes

Reaction equation

HRID 1590387 reaction equation
C([O:5][C:6]([C@H:8]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]1([CH3:22])[CH3:21])=O)CCC.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl>[F:18][C:17]([F:19])([F:20])[C:13]1[CH:12]=[C:11]([C@H:10]2[C@H:8]([CH2:6][OH:5])[C:9]2([CH3:21])[CH3:22])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 86746725(+/-)-n-Butyl-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]-formate

Product 1

HCID 131717855(+/-)-[trans-3-(3-Trifluoromethylphenyl)-2,2-dimethylcyclopropyl]methanolYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above ester (0.78 g) was dissolved in dichloromethane (12 ml) under nitrogen and cooled to -20°. Diisobutylaluminium hydride (7.4 ml) was added dropwise and the solution stirred at 25° for 18 hours. Careful addition of dilute hydrochloric acid was followed by work up in the usual manner to give (±)-[trans-3-(3-trifluoromethylphenyl)-2,2-dimethylcyclopropyl]methanol (0.31 g). NMR 1H: 7.5(4H,m), 3.65(2H,d), 2.55(1H,bs), 1.62(1H,d), 1.14(1H,m), 1.15(3H,s). 0.90(3H,s).

Workup

  1. temperaturecooled to -20°

Sources & evidence

ORD record
ord-6058b30e61794a71b1b0b671b46190e5
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

Loading…