3,3-Dimethylbutanoyl chloride → 3,3-Dimethyl-1-(2-thienyl)-1-butanone
Reaction equation
[C:1]([CH2:5][C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)CCC>C1(C)C=CC=CC=1.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:2][C:1]([CH3:4])([CH3:3])[CH2:5][C:6]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:7]Participants
6
Procedure
A mixture of t-butylacetyl chloride (1 ml, 7.2 mmol), 2-(tributylstannyl)thiophene (2.4 ml, 7.56 mmol) and PdCl2(PPh3)2 (98 mg, 0.14 mmol) in toluene (50 ml) was heated at reflux until the starting material disappeared. After cooling at room temperature, the brown-black solution was diluted with ether and washed with a 0.1 N aqueous HCl solution. The organic phase was separated and stirred vigorously with a 10% w/v aqueous KF solution for 30 minutes. After filtration, the layers were separated and the organic one washed with water, brine, dried over MgSO4 and concentrated. The residual brown oil was chromatographied on silica gel (hexane/AcOEt 97/3) to give 3,3-dimethyl-1-(2-thienyl)-1-butanone 10 as a colorless oil (810 mg, 62%).
Workup
- temperaturewas heated
- temperatureat reflux until the starting material
- washwashed with a 0.1 N aqueous HCl solution
- customThe organic phase was separated
- filtrationAfter filtration
- customthe layers were separated
- washthe organic one washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e47b32a9f3ad4cc89b540c0f0a637fc8
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361668B2
Reaction notes
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