Water → HCID 59133000, compound

HRID 1993142Notes

Reaction equation

HRID 1993142 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 2600 mL of THF, and was cooled to −10° C. while keeping the internal temperature, 313.2 g of potassium-t-butoxide was added thereto. While keeping the internal temperature, the solution was stirred for 1 hour, and then THF (800 mL) solution containing 200.0 g of bicyclohexyl-4,4′-dione was added dropwise. While keeping the internal temperature, the solution was stirred for 1 hour, and then water was added to stop the reaction. The solvent was evaporated under reduced pressure. Then, the residue was added with hexane, was vigorously stirred, and was subjected to filtration (twice). The resultant product was mixed with the filtrate, then washed with 50% methanol aqueous solution and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to obtain 231.8 g of a white solid.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. stirringthe solution was stirred for 1 hour
  4. customthe reaction
  5. customThe solvent was evaporated under reduced pressure
  6. additionThen, the residue was added with hexane
  7. stirringwas vigorously stirred
  8. filtrationwas subjected to filtration (twice)
  9. additionThe resultant product was mixed with the filtrate
  10. washwashed with 50% methanol aqueous solution and saturated saline in this order
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated

Sources & evidence

ORD record
ord-07c725ceb1df422f875bdf27c2423580
Source dataset
uspto-grants-2010_01
Patent number
US07651630B2

Reaction notes

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