LY88074 Trimethyl ether → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 234790노트

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HRID 234790 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:8][C:7]=2[CH:29]=1.C(S)C.[Na]>CN(C=O)C.O.CCOC(C)=O.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:8][C:7]=2[CH:29]=1

참가 물질

7

반응물 2

HCID 9953060LY88074 Trimethyl etherHCID 45051917HCID 45051917, 화합물

생성물 1

HCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A solution of 0.4 g (1 mmol) of [6-Methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl][4-methoxyphenyl]methanone in 2 mL of DMF was added to a solution of 3 mL of 0.5M sodium ethanethiol in DMF. The reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was allowed to cool and diluted with 10 mL of water and 10 mL of EtOAc and neutralized with 1N HCl. The reaction mixture was extracted three times with 30 mL portions of EtOAc. The combined organic extracts were washed four times with 20 mL portions of brine and dried with MgSO4 and evaporated to dryness. The crude product was chromatographed on silica eluting with 30% EtOAc in hexane, and evaporated to dryness. This yielded 0.31 g of the title compound as a yellow solid.

후처리

  1. temperatureto cool
  2. extractionThe reaction mixture was extracted three times with 30 mL portions of EtOAc
  3. washThe combined organic extracts were washed four times with 20 mL portions of brine
  4. dry with materialdried with MgSO4
  5. customevaporated to dryness
  6. customThe crude product was chromatographed on silica eluting with 30% EtOAc in hexane
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-7df6a894b87446858f7b70e9573da166
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596106

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