Benzo(B)Thiophene → 1-Benzo[b]thien-2-yl-1-propanone

HRID 2183601ノート

反応式

HRID 2183601 の反応式
C([Li])CCC.[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]1=2.CON(C)[C:18](=[O:21])[CH2:19][CH3:20].[Cl-].[NH4+]>CCOCC.O.C(OCC)(=O)C>[S:6]1[C:10]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]1=2

参加物

8

反応物 4

HCID 7221Benzo(B)ThiopheneHCID 25517Ammonium ChlorideHCID 11344007N-Methoxy-N-methylpropionamideHCID 178418339Butyllithium

生成物 1

HCID 224742131-Benzo[b]thien-2-yl-1-propanone収率 80.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

n-Butyllithium (1.6 M solution in hexanes; 28.9 ml) was added dropwise under nitrogen at 0° C. to a stirred solution of benzo[b]thiophene (6.21 g) in ether (90 ml), then the mixture was stirred 0° C. for 15 minutes and cooled to −70° C. A solution of N-methoxy-N-methylpropionamide (5.42 g) in ether (40 ml) was added over 10 minutes, then the mixture was allowed to warm to ambient temperature and was stirred at ambient temperature for 3.5 hours. The mixture was poured into saturated aqueous ammonium chloride solution (200 ml) and ethyl acetate (100 ml) and water (50 ml) were added. The organic phase was separated, washed with saturated aqueous sodium chloride solution (150 ml), dried (Na2SO4) and the solvents were removed in vacua. The residue was triturated with petroleum ether (b.p. 40-60° C.) (25 ml) and the resulting solid was collected by filtration and dried in vacuo to give 1-(benzo[b]thiophen-2-yl)propan-1-one (7.05 g) as a colourless solid, m.p. 79-81° C.

後処理

  1. temperaturecooled to −70° C
  2. temperatureto warm to ambient temperature
  3. stirringwas stirred at ambient temperature for 3.5 hours
  4. additionwere added
  5. customThe organic phase was separated
  6. washwashed with saturated aqueous sodium chloride solution (150 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvents were removed in vacua
  9. customThe residue was triturated with petroleum ether (b.p. 40-60° C.) (25 ml)
  10. filtrationthe resulting solid was collected by filtration
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-fdcbc5da3ff945e88f44e5aa4bc764fe
出典データセット
uspto-grants-2005_05
特許番号
US06900216B2

反応ノート

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