Water → HCID 67082453, compound

HRID 1943552Notes

Reaction equation

HRID 1943552 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]([CH:35]1[CH2:40][CH2:39][C:38]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([F:54])[C:49]=2[F:55])([CH:41]2[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:31][CH2:32][CH2:33][CH3:34].O>C1COCC1.C1(C)C=CC=CC=1>[CH2:30]([CH:35]1[CH2:36][CH2:37][C:38]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([F:54])[C:49]=2[F:55])([CH:41]2[CH2:42][CH2:43][C:44](=[CH:2][O:3][CH3:4])[CH2:45][CH2:46]2)[CH2:39][CH2:40]1)[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 67082441HCID 67082441, compound

Product 1

HCID 67082453HCID 67082453, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

Well-dried methoxymethyltriphenylphosphonium chloride (8.6 g) and THF (100 ml) were mixed under a nitrogen atmosphere, and cooled to −30° C. Then, potassium t-butoxide (t-BuOK; 2.8 g) was put in thereto in twice in the temperature range of −30° C. to −20° C. After the mixture had been stirred at −20° C. for 30 minutes, the compound (38) (7.6 g) dissolved in THF (100 ml) was added dropwise thereto in the temperature range of −30° C. to −20° C. After the reaction mixture had been stirred at −10° C. for 30 minutes, it was poured into a mixture of water (200 ml) and toluene (200 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The eluent obtained was concentrated under reduced pressure, giving 8.1 g of 1-[4-pentyl-(2,3-difluorophenyl)cyclohexyl]-4-methoxymethylenecyclohexane (39). The yield based on the compound (38) was 99.0%.

Workup

  1. customtwice in the temperature range of −30° C. to −20° C
  2. additionwas added dropwise
  3. customin the temperature range of −30° C. to −20° C
  4. stirringAfter the reaction mixture had been stirred at −10° C. for 30 minutes
  5. additionmixed
  6. customhad separated into two phases of organic and
  7. extractionaqueous phases, and extraction into an organic phase
  8. customThe organic phase obtained
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solution obtained
  12. concentrationwas concentrated under reduced pressure
  13. customthe residue obtained
  14. customwas purified with a fractional operation by means of column chromatography
  15. customThe eluent obtained
  16. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e5d792e7e6349f0aa8dae14348f8e5a
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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