Acetic Acid → HCID 66702093, compound

HRID 424396Notes

Reaction equation

HRID 424396 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.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]([C:8](=[CH:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[CH:17]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 680093-FluorobenzaldehydeHCID 58245831Ethyl 5-bromo-β-oxo-2-thiophenepropanoate

Product 1

HCID 66702093HCID 66702093, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 3-(5-bromothiophen-2-yl)-3-oxopropanoate (2.456 g, 8.86 mmol, from Preparation 1, Step 1), 3-fluorobenzaldehyde (1.034 ml, 9.75 mmol), piperidine (0.088 ml, 0.886 mmol) and acetic acid (0.389 ml, 6.8 mmol) in benzene (50 ml) was heated at 85° C. for 6 h using a Dean-Stark trap to remove the formed water. The reaction solution was concentrated. The crude product was dissolved in a small amount of toluene and charged to 80 g silica gel cartridge which was eluted with a 15 min gradient from 0-5% ethyl acetate in hexane to give ethyl 2-(5-bromothiophene-2-carbonyl)-3-(3-fluorophenyl)acrylate as a viscous yellow oil (3.33 g). HPLC: Rt 3.728 min (Method A); LCMS m/z 407.02, 405.02 (M+23)

Workup

  1. customto remove the formed water
  2. concentrationThe reaction solution was concentrated
  3. dissolutionThe crude product was dissolved in a small amount of toluene
  4. additioncharged to 80 g silica gel cartridge which
  5. washwas eluted with a 15 min gradient from 0-5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9b4f077365314aaaa5040d90c291f6ef
Source dataset
uspto-grants-2012_01
Patent number
US08106046B2

Reaction notes

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