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Sodium hydride → tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylate

HRID 1667308
Notes
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Reaction equation

HRID 1667308 reaction equation
[H-].[Na+].[Cl-].[Cl:4][C:5]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:6]=1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:32]([CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1)=O.[Cl-].[NH4+]>CS(C)=O>[Cl:4][C:5]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:6]=1/[CH:7]=[CH:32]/[CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:41])[CH2:36][CH2:35]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 86612298(2-Chloro-6-methylbenzyl)(triphenyl)phosphonium chloride

Product 1

HCID 10088346tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylateYield 41.2%

Reagents, catalysts & solvents

1
HCID 679Dimethyl SulfoxideSolvent

Procedure

264 mg of sodium hydride (55%) was added to a solution of 2.65 g of (2-chloro-6-methylbenzyl)(triphenyl)phosphonium chloride in 20 ml of dimethylsulfoxide, followed by stirring at ambient temperature for 1 hour. After 994 mg of tert-butyl 4-formylpiperidine-1-carboxylate was added to the reaction mixture, the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 645 mg of tert-butyl 4-[(E)-2-(2-chloro-6-methylphenyl)vinyl]piperidine-1-carboxylate as an oil.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-03f1f2baaaac4708b07d89e49e4052f2
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044206B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes