Water → 4-(4-Butoxy-2,3-difluorophenyl)-4'-methoxymethylene-bicyclohexyl

HRID 1886722Notes

Reaction equation

HRID 1886722 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:46][CH2:45][CH:44]([CH:47]3[CH2:52][CH2:51][C:50](=O)[CH2:49][CH2:48]3)[CH2:43][CH2:42]2)=[C:37]([F:54])[C:36]=1[F:55])[CH2:31][CH2:32][CH3:33].O>C1COCC1.C1(C)C=CC=CC=1>[CH2:30]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:42][CH2:43][CH:44]([CH:47]3[CH2:52][CH2:51][C:50](=[CH:2][O:3][CH3:4])[CH2:49][CH2:48]3)[CH2:45][CH2:46]2)=[C:37]([F:54])[C:36]=1[F:55])[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 666837754'-(4-Butoxy-2,3-difluorophenyl)-bicyclohexyl-4-one

Product 1

HCID 666827514-(4-Butoxy-2,3-difluorophenyl)-4'-methoxymethylene-bicyclohexylYield 98.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

Well-dried methoxymethyltriphenylphosphonium chloride (7.9 g) and THF (100 ml) were mixed under an atmosphere of nitrogen, and cooled to −30° C. Then, potassium t-butoxide (t-BuOK) (2.6 g) was added in four portions in the temperature range of −30° C. to −20° C. After the stirring at −20° C. for another 30 minutes, the compound (24) (6.8 g) dissolved in THF (35 ml) was added dropwise in the temperature range of −30 to −20° C. After the mixture had been stirred at −10° C. for 30 minutes, the reaction solution was poured into a mixture water (200 ml) and toluene (100 ml) and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed with water and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure and the resulting residue was purified with a fractional operation by means of column chromatography using silica gel as a stationary phase powder and toluene as an eluent. The resulting eluent was concentrated under reduced pressure to leave 4-(4-butoxy-2,3-difluorophenyl)-4′-methoxymethylene-bicyclohexyl (25) (7.2 g). The yield based on the compound (24) was 95.5%.

Workup

  1. additionwas added dropwise in the temperature range of −30 to −20° C
  2. additionmixed with it
  3. customhad separated into two phases of organic and aqueous phases
  4. extractionthe extraction into an organic phase
  5. customThe resulting organic phase was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customthe resulting residue was purified with a fractional operation by means of column chromatography
  10. concentrationThe resulting eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a36237759dc54a10980751a29ba6c9f0
Source dataset
uspto-grants-2013_08
Patent number
US08501038B2

Reaction notes

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