Propyltriphenylphosphonium bromide → (1R,S) 1,2,2-trimethyl-3-(2-pentenyl)-cyclopentanol

Reaction equation

[CH3:1][C:2]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4](O)[O:3]2.[Br-].[C:14]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CCC)[CH:19]=CC=C[CH:15]=1>>[CH3:1][C@@:2]1([OH:3])[CH2:8][CH2:7][C@@H:6]([CH2:5][CH:4]=[CH:15][CH2:14][CH3:19])[C:9]1([CH3:11])[CH3:10]

Participants

Reactant 2

HCID 80374Propyltriphenylphosphonium bromide

HCID 543125041,8,8-Trimethyl-2-oxa bicyclo [3,2,1] octan-3-ol

Product 1

HCID 70474476(1R,S) 1,2,2-trimethyl-3-(2-pentenyl)-cyclopentanolYield 69.4%

Procedure

Using the procedure of Example 7, 5 g of 1,8,8-trimethyl-2-oxa bicyclo [3,2,1] octan-3-ol and 15 g of triphenyl propyl phosphonium bromide were reacted and the product was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 4 g of (1R,S) 1,2,2-trimethyl-3-(2-pentenyl)-cyclopentanol.

Workup

customwere reacted
customthe product was chromatographed over silica gel
washwas eluted with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-a06c5989b76b48efb386e573d26ffc28
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04501687

Reaction notes

Loading…