Water → HCID 54151335, compound

HRID 2376302Notes

Reaction equation

HRID 2376302 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[Na+].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[OH2:16]>CN(C=O)C>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[C:2]([CH3:5])[CH2:3][OH:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 707414-BromobenzaldehydeHCID 23676156Sodium t-butoxide

Product 1

HCID 54151335HCID 54151335, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium tert-butoxide (10.6 g, 110 mmol) in DMF (60 mL) was added triethyl phosphonoacetate (26.2 g, 110 mmol) under argon atmosphere at −10° C. and the mixture was stirred at the same temperature for 1 hour. 4-bromobenzaldehyde (18.5 g, 100 mmol) was added to the solution at 10° C. or lower, and the mixture was warmed to room temperature, and then stirred for 2 hours. Water was added to the reaction solution after ice-cooling, which was extracted with toluene. The extract was washed with a saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The obtained oily matter was dissolved in toluene (200 mL), dihydrobis(2-methoxyethoxy) sodium aluminate (a 70% toluene solution, 41.5 g, 144 mmol) was added dropwise at −10° C., and then the mixture was stirred at the same temperature for 1 hour. A 10% aqueous potassium sodium tartrate solution was added to separate the organic layer. The organic layer was washed with a 10% aqueous potassium sodium tartrate solution and a saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 20.1 g (yield 88%) of the title compound as an oily matter.

Workup

  1. stirringstirred for 2 hours
  2. temperaturecooling
  3. extractionwhich was extracted with toluene
  4. washThe extract was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe obtained oily matter was dissolved in toluene (200 mL)
  8. additiondihydrobis(2-methoxyethoxy) sodium aluminate (a 70% toluene solution, 41.5 g, 144 mmol) was added dropwise at −10° C.
  9. stirringthe mixture was stirred at the same temperature for 1 hour
  10. additionA 10% aqueous potassium sodium tartrate solution was added
  11. customto separate the organic layer
  12. washThe organic layer was washed with a 10% aqueous potassium sodium tartrate solution
  13. dry with materiala saturated brine, dried over sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-721eeba7610344a3932de161b6fc3b8b
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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