4-Phenyl-5-propyl-thiophene-2-carboxylic acid methoxy-methyl-amide → 1-(4-Phenyl-5-propyl-thiophen-2-yl)-ethanone

HRID 552296Notes

Reaction equation

HRID 552296 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[S:10][C:11]([CH2:20][CH2:21][CH3:22])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)=[O:8]>O>[C:14]1([C:12]2[CH:13]=[C:9]([C:7](=[O:8])[CH3:1])[S:10][C:11]=2[CH2:20][CH2:21][CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 866401764-Phenyl-5-propyl-thiophene-2-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, compound

Product 1

HCID 671651301-(4-Phenyl-5-propyl-thiophen-2-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 2° C. methylmagnesium bromide (1 mL, 1.7 M in THF) is added to a solution of 4-phenyl-5-propyl-thiophene-2-carboxylic acid methoxy-methyl-amide (900 mg, 3.11 mmol). The mixture stirred for 1 h before another portion (0.2 mL) of the Grignard reagent is added. Stirring is continued for 2 h. The mixture is diluted with water, extracted with EA and the organic extracts are dried over MgSO4 and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 5:4 to give 1-(4-phenyl-5-propyl-thiophen-2-yl)-ethanone (456 mg) as a yellow oil; LC-MS: tR=1.06 min, [M+1]+=245.14, 1H NMR (CDCl3): δ 7.59 (s, 1H), 7.47-7.32 (m, 5H), 2.87-2.81 (m, 2H), 2.54 (s, 3H), 1.76-1.63 (m, 2H), 0.95 (t, J=/.6 Hz, 3H).

Workup

  1. additionis added
  2. extractionextracted with EA
  3. dry with materialthe organic extracts are dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 5:4

Sources & evidence

ORD record
ord-7876e186fdaf45a286fdfbc5478001ef
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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