Ethanol → 5-(4-Ethoxy-2,3-difluorophenyl)-2-pentylcyclohexanol

HRID 1016234Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH2:11]2)=[C:6]([F:21])[C:5]=1[F:22])[CH3:2].C([OH:25])C.[OH-].[Na+].OO>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([OH:25])[CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)=[C:6]([F:21])[C:5]=1[F:22])[CH3:2]

Participants

Conditions

Temperature: 2 °C

Procedure

53 g of 1-ethoxy-2,3-difluoro-4-(4-pentylcyclohex-3-enyl)benzene were dissolved in 500 ml of THF, and the mixture was cooled to 2° C. 195 ml of borane/THF complex were subsequently added dropwise over the course of 30 minutes with stirring. After the mixture had been stirred for a further 2 hours, 48 ml of ethanol were added dropwise to the solution at RT. Subsequently, firstly a solution of 10.6 g of sodium hydroxide and then 63 ml of 30% hydrogen peroxide were added dropwise. The mixture was subsequently refluxed for 2 hours and subjected to conventional work-up, giving 5-(4-ethoxy-2,3-difluorophenyl)-2-pentylcyclohexanol.

Workup

addition195 ml of borane/THF complex were subsequently added dropwise over the course of 30 minutes
stirringAfter the mixture had been stirred for a further 2 hours
temperatureThe mixture was subsequently refluxed for 2 hours

Sources & evidence

ORD record: ord-ba3a7ae1c2e04acb894d94cdd25ed2c2
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06475595B1

Reaction notes

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