Water → HCID 59367762, compound

HRID 1643481Notes

Reaction equation

HRID 1643481 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH:21]=O)(=[O:14])=[O:13])=[C:7]([CH3:23])[CH:6]=1.[OH2:24].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH3:23])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2/[CH:21]=[CH:26]/[C:27]([O:28][CH2:29][CH3:25])=[O:24])(=[O:13])=[O:14])=[C:9]([CH3:11])[CH:10]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 59367724HCID 59367724, compound

Product 1

HCID 59367762HCID 59367762, compoundYield 40%

Procedure

A solution of triethyl phosphonoacetate (3.8 mmol, 1.2 eq) in THF (12 ml) was added dropwise to a suspension of NaH (3.8 mmol, 1.2 eq) in THF (12 ml) at 0° C. and the mixture was stirred for 30 min. 1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidine-2-carbaldehyde (3.2 mmol) in THF (6 ml) was then added and the mixture was stirred for a further 30 min. The reaction mixture was warmed to room temperature and stirred for 12 h. Hydrolysis was then carried out with water and the mixture was extracted with ethyl acetate. The organic phase was washed with water (20 ml) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (5-20% ethyl acetate in hexane). Yield: 40%

Workup

  1. stirringthe mixture was stirred for a further 30 min
  2. stirringstirred for 12 h
  3. customHydrolysis
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water (20 ml) and saturated sodium chloride solution (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (5-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ca6bfe73ff844feba32581769342cfc2
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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