2-Ethylhexanoylmethylenetriphenylphosphorane → 2-(7-Hydroxyheptyl)-3-(4-ethyl-3-oxo-1-octenyl)cyclopentanol

HRID 1581108Notes

Reaction equation

[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH:3]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[CH2:17]([CH:19]([CH2:42][CH2:43][CH2:44][CH3:45])[C:20]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21])[CH3:18]>O1CCCC1>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:3]1[CH:4]([CH:7]=[CH:22][C:20](=[O:21])[CH:19]([CH2:17][CH3:18])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:5][CH2:6][CH:2]1[OH:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 3-hydroxy-2-(7-hydroxyheptyl)-cyclopentanecarbaldehyde (6 g.) [prepared as described in Example 1]and 2-ethylhexanoylmethylenetriphenylphosphorane (9g.) in dry tetrahydrofuran (70 ml.) was heated under refux under nitrogen for 6 hours. The solvent was removed in vacuo and the residue was triturated with petrol (b.p. 40°-α°C.) with cooling to 0°C. and filtered to remove triphenylphosphine oxide. Evaporation of the filtrate then gave crude 2-(7-hydroxyheptyl)-3-(4-ethyl-3-oxo-1-octenyl)cyclopentanol (4.4 g.), ν max 1620 cm-1, 1655 cm-1 (liquid film), which was used in the next step without further purification.

Workup

customprepared
temperaturewas heated under refux under nitrogen for 6 hours
customThe solvent was removed in vacuo
customthe residue was triturated with petrol (b.p. 40°-α°C.)
filtrationfiltered
customto remove triphenylphosphine oxide
customEvaporation of the filtrate

Sources & evidence

ORD record: ord-a51974f7273545eb9bf3046007e17c1d
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03935261

Reaction notes

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