Benzo(B)Thiophene → 2-(Dimethoxyacetyl)benzothiophene

HRID 34738

反応式

HRID 34738 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[CH3:15][O:16][CH:17]([O:26][CH3:27])[C:18](N1CCOCC1)=[O:19]>C1COCC1>[CH3:15][O:16][CH:17]([O:26][CH3:27])[C:18]([C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)=[O:19]

参加物

5

反応物 3

HCID 7221Benzo(B)ThiopheneHCID 21298597N-(dimethoxyacetyl)morpholineHCID 178418339Butyllithium

生成物 1

HCID 142769322-(Dimethoxyacetyl)benzothiophene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of benzothiophene (7.11 g., 0.053 mol) in 120 ml. dry THF was cooled to 0°. Butyl lithium (35.3 ml. of 1.5M in hexane, 0.053 mol) was added dropwise, maintaining 0°-5°, and the mixture then warmed to ambient temperature for 1.25 hours, cooled to -75° C. and N-(dimethoxyacetyl)morpholine (10.0 g., 0.053 mol) in 50 ml. dry THF added dropwise maintaining -75° to -70°. The reaction was quenched by adding to 300 ml. saturated NH4Cl and 300 ml. ether. The organic layer was separated, washed with brine, dried over MgSO4 and stripped to an oil, 14 g., which was distilled to yield purified title product, 8.00 g., bp 137°-139°/0.25 mm.; tlc Rf 0.23 (6:1 hexane:ethyl acetate), 0.47 (2:1 hexane:ethyl acetate); 1H-nmr 3.6 (s, 6H), 5.2 (s, 1H), 7.3-7.6 (m, 2H), 7.8-8.05 (m, 2H), 8.4 (s, 1H), tlc Rf 0.31 (4:1 hexane:ethyl acetate), 0.47 (2:1 hexane:ethyl acetate).

後処理

  1. temperaturemaintaining 0°-5°
  2. temperaturecooled to -75° C.
  3. temperaturemaintaining -75° to -70°
  4. customThe reaction was quenched
  5. additionby adding to 300 ml
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. distillation, which was distilled
  10. customto yield
  11. custompurified title product, 8.00 g

出典と根拠

ORDレコード
ord-92c875558a0a424189ef189c8a798b96
出典データセット
uspto-grants-1988_08
特許番号
US04762921

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