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

HRID 34738

반응식

HRID 34738 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 142769322-(Dimethoxyacetyl)benzothiophene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-92c875558a0a424189ef189c8a798b96
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762921

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