Ethyl 2-(diphenylmethyleneamino)acetate → ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 1800796Notes

Reaction equation

HRID 1800796 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Cs+].Br[CH2:25][CH:26]=[C:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]1([C:7](=[N:8][CH:9]([CH2:25][CH:26]=[C:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 219961434-(2-Bromoethylidene)tetrahydro-2H-pyranHCID 23679066Caesium hydroxide--water (1/1/1)

Product 1

HCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-(diphenylmethylidene)glycinate (5.29 g, 19.8 mmol), benzyltriethylammonium chloride (0.41 g, 1.8 mmol) and cesium hydroxide monohydrate (4.54 g, 27.0 mmol) in anhydrous dichloromethane (50 mL) was added 4-(2-bromoethylidene)tetrahydro-2H-pyran (3.44 g, 18.0 mmol) as a solution in anhydrous dichloromethane (40 mL) and the reaction stirred at room temperature for 72 h under nitrogen. The reaction was partitioned between dichloromethane and water and the aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5-40% hexanes/EtOAc to afford the title compound as a clear oil in quantitative yield.

Workup

  1. customThe reaction was partitioned between dichloromethane and water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 5-40% hexanes/EtOAc

Sources & evidence

ORD record
ord-8b3255e4f3e64cc0b898972109996219
Source dataset
uspto-grants-2013_01
Patent number
US08344155B2

Reaction notes

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