Water → 4-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-4'-propoxybicyclohexane

HRID 1095241Notes

Reaction equation

HRID 1095241 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1.[H-].[Na+].O.[C:35]1(C)[CH:40]=CC=C[CH:36]=1>BrCCC.CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:26][CH2:27][CH:28]([O:31][CH2:36][CH2:35][CH3:40])[CH2:29][CH2:30]2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 24758Sodium hydrideHCID 667814604'-(2-Fluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-ol

Product 1

HCID 667815584-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-4'-propoxybicyclohexane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 78401-BromopropaneSolvent

Conditions

Temperature
60 °C

Procedure

The compound (15) (8.2 g), dimethyl sulfoxide (40 ml) and sodium hydride (1.0 g) were put in a reaction vessel under a nitrogen atmosphere, and heated to 60° C. The stirring was continued for 1 hour, and then a dimethyl sulfoxide solution in which 1-bromopropane (16) (2.6 g) was dissolved in dimethyl sulfoxide (5 ml) was added dropwise thereto, and the mixture was heated to 120° C. The stirring was continued for 2 hours, and then the mixture was cooled slowly to room temperature, and water (200 ml) and toluene (200 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with water and a saturated aqueous solution of sodium hydrogencarbonate and brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using toluene as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume) and dried, giving 2.8 g of 4-[2-fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-4′-propoxybicyclohexane (No. 54). The yield based on the compound (12) was 31.4%.

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated to 120° C
  3. waitThe stirring was continued for 2 hours
  4. temperaturethe mixture was cooled slowly to room temperature
  5. additionmixed
  6. customhad separated into two phases
  7. washwashed sequentially with water
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and brine, and then dried over anhydrous magnesium sulfate
  9. concentrationThe solution was concentrated under reduced pressure
  10. customthe residue was purified with a fractional operation by means of column chromatography
  11. customsilica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume)
  12. customdried

Sources & evidence

ORD record
ord-9ba68b2c683d449d9ea47747a10f86dd
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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