Dimethylformamide → Propan-2-yl 3-(2-fluorophenyl)prop-2-enoate

HRID 421293

Reaction equation

HRID 421293 reaction equation
[H-].[Na+].[Br-].[CH2:4]([O:6][C:7]([CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])[CH3:5].[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O.[CH3:38]N(C=O)C>C(OCC)(=O)C>[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1/[CH:32]=[CH:9]/[C:7]([O:6][CH:4]([CH3:5])[CH3:38])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67970o-FluorobenzaldehydeHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromide

Product 1

HCID 57870847Propan-2-yl 3-(2-fluorophenyl)prop-2-enoateYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

400 mg of sodium hydride (60% in oil, 10 mmol) were added to a stirred solution of 4.4 g of ethoxycarbonylmethyltriphenylphosphonium bromide (10 mmol) in 20 ml of DMF and the mixture was stirred further at RT for 10 min. 1.24 g of 2-fluoro-benzaldehyde (10 mmol) were added and the mixture was stirred for 5 h at RT. The reaction mixture was taken up in 100 ml of ethyl acetate and washed with a common salt solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification took place using a silica gel chromatography (ethyl acetate/heptane 1:1). 1.25 g of the title compound were obtained. Yield: 60%.

Workup

  1. stirringthe mixture was stirred for 5 h at RT
  2. washwashed with a common salt solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-964fca885af645dab3e1b47b2191ea3b
Source dataset
uspto-grants-2012_01
Patent number
US08097758B2

Linked notes

Loading…