Water → HCID 59133000, compound

HRID 2241795Notes

Reaction equation

HRID 2241795 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+].[CH:30]1([CH:37]2[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]2)[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1.O.C1[CH2:49][O:48][CH2:47]C1>>[CH3:2][O:3][CH:4]=[C:33]1[CH2:34][CH2:35][CH:30]([CH:37]2[CH2:42][CH2:41][C:40](=[CH:47][O:48][CH3:49])[CH2:39][CH2:38]2)[CH2:31][CH2:32]1

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 2648254,4'-BicyclohexanoneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 59133000HCID 59133000, compound

Conditions

Temperature
-10 °C

Procedure

882.3 g of methoxymethyltriphenylphosphonium chloride was dispersed in 2,600 mL of THF, followed by cooling to −10° C. 313.2 g of potassium-t-butoxide were added while maintaining the inner temperature. After stirring or one hours, a THF (800 mL) solution of 200.0 g of bicyclohexyl-4,4′-dione was and added dropwise. After stirring for 1 hour while maintaining the inner temperature, water was added thereby terminating the reaction. The solvent was distilled off under reduced pressure and hexane was added, followed by stirring and vigorous stirring and further filtration (twice). The filtrates were combined, washed in turn with an aqueous 50% methanol solution and saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 231.8 g of a white solid.

Workup

  1. temperaturewhile maintaining the inner temperature
  2. additionadded dropwise
  3. stirringAfter stirring for 1 hour
  4. additionwas added
  5. customthereby terminating
  6. customthe reaction
  7. distillationThe solvent was distilled off under reduced pressure and hexane
  8. additionwas added
  9. stirringby stirring
  10. stirringvigorous stirring
  11. filtrationfurther filtration (twice)
  12. washwashed in turn with an aqueous 50% methanol solution and saturated saline
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4ee55c6b5ab54a33a9ebaaaf8213b068
Source dataset
uspto-grants-2010_03
Patent number
US07670504B2

Reaction notes

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