Potassium Carbonate → HCID 86583532, compound

HRID 1066594Notes

Reaction equation

HRID 1066594 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH:21]=O)[CH:18]=[C:17]([CH:23]=[O:24])[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[C:25](=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CN(C=O)C.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH:21]=[CH2:25])[CH:18]=[C:17]([CH:23]=[O:24])[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 86583533HCID 86583533, compound

Product 1

HCID 86583532HCID 86583532, compoundYield 45.9%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.87 g of methyl (RS)-(4-cyano-phenylamino)-(3,5-diformyl-phenyl)-acetate in 20 ml of dioxan and 1.3 ml of DMF was treated with 3.18 g of methyltriphenylphosphonium bromid and 1.84 g of potassium carbonate. The suspension was heated for 3 days to 100° C. It was left to cool to room temperature, filtered and concentrated. The crude product was isolated by extraction isoliert and purified by chromatography on silica gel. There were obtained 1.31 g of methyl (RS)-(4-cyano-phenylamino)-(3-formyl-5-vinyl-phenyl)-acetate as a light yellow solid.

Workup

  1. temperatureThe suspension was heated for 3 days to 100° C
  2. waitIt was left
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was isolated by extraction isoliert
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-7429b37f845944479c5f9614e0dbe6a8
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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