Water → HCID 178501080, compound

HRID 926997Notes

Reaction equation

HRID 926997 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[CH:34]([C@@H:36]1[CH2:41][CH2:40][C@H:39]([C:42]([O:44][CH3:45])=[O:43])[CH2:38][CH2:37]1)=O.O>C1COCC1>[C:3]1(/[CH:2]=[CH:34]/[C@@H:36]2[CH2:41][CH2:40][C@H:39]([C:42]([O:44][CH3:45])=[O:43])[CH2:38][CH2:37]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2734970Benzyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 178501145HCID 178501145, compound

Product 1

HCID 178501080HCID 178501080, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzyltriphenylphosphonium bromide (2.94 g) was dissolved in THF (23.0 mL), added at −20° C. with potassium tert-butoxide (1.07 g) in small portions, and stirred for 1 hour at the same temperature. Subsequently, a THF (6.0 mL) solution of methyl cis-4-formylcyclohexane carboxylate (1.00 g) was added dropwise over 35 minutes, and stirred for 1.6 hours at the same temperature. After raising the temperature to room temperature, it was stirred after adding water and extracted with toluene. The organic layer was washed with water and saturated brine in order. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (9% ethyl acetate/hexane) to obtain the title compound (268 mg) as a colorless oil.

Workup

  1. stirringstirred for 1.6 hours at the same temperature
  2. stirringit was stirred
  3. extractionextracted with toluene
  4. washThe organic layer was washed with water and saturated brine in order
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residues were purified by silica gel column chromatography (9% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bd73194540a4416eb9c7c787dc6bd12f
Source dataset
uspto-grants-2016_03
Patent number
US09290440B2

Reaction notes

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