Isopropyltriphenylphosphonium iodide → (1R,S) 1,2,2-trimethyl-3-(3-methyl-2-butenyl)-cyclopentanol

HRID 615840Notes

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.[I-].[C:14]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C(C)C)[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]=[C:14]([CH3:19])[CH3:15])[C:9]1([CH3:11])[CH3:10]

Participants

Reactant 2

HCID 2723783Isopropyltriphenylphosphonium iodide

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

Product 1

HCID 70473477(1R,S) 1,2,2-trimethyl-3-(3-methyl-2-butenyl)-cyclopentanolYield 71.1%

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 isopropyl phosphonium iodide were reacted and the product was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 4.1 g of (1R,S) 1,2,2-trimethyl-3-(3-methyl-2-butenyl)-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-7b083012fb254136b47709c9572a41ad
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04501687

Reaction notes

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