Acetic Acid → HCID 66702189, compound

HRID 424394Notes

Reaction equation

HRID 424394 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.N1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:21](O)(=O)[CH3:22]>C1C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]([C:8](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 58245831Ethyl 5-bromo-β-oxo-2-thiophenepropanoate

Product 1

HCID 66702189HCID 66702189, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 3-(5-bromothiophen-2-yl)-3-oxopropanoate (3.73 g, 13.46 mmol), benaldehyde (1.501 ml, 14.81 mmol), piperidine (0.133 ml, 1.346 mmol) and acetic acid (0.389 ml, 6.8 mmol) in benzene (50 ml) was heated at 85° C. for 5 h using a Dean-Stark trap for removal of the water formed. The reaction solution was concentrated. The resulting residue was purified via flash chromatography (silica gel cartridge with eluent of 0-5% ethyl acetate/hexane) to give ethyl 2-(5-bromothiophene-2-carbonyl)-3-phenylacrylate as a light amble viscous oil (4.25 g). LCMS m/z 388.99, 390.09 (M+23); HPLC: Rt 3.701 min.

Workup

  1. customfor removal of the water
  2. customformed
  3. concentrationThe reaction solution was concentrated
  4. customThe resulting residue was purified via flash chromatography (silica gel cartridge with eluent of 0-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-22e092769cad498ea14b96abdb0c3291
Source dataset
uspto-grants-2012_01
Patent number
US08106046B2

Reaction notes

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