Hydrochloric Acid → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 354085

반응식

HRID 354085 반응식
C(S)C.C([Li])CCC.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1.Cl>O1CCCC1.CN(C)C=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 9953060LY88074 Trimethyl etherHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethanethiol (538 mL, 7.27 mmol) in 1.88 mL of tetrahydrofuran, cooled to −30° C. was added n-butyllithium (2.57 mL, 2.5 M, 6.42 mmol) and the reaction was warmed to room temperature. Dimethylformamide (1 mL) was added then the product from Step 1 (1.73 g, 4.3 mmol) in 2.7 mL of dimethylformamide. The reaction was heated at 58° C. for two hours then at 80° C. for 1 hour. The cooled reaction was poured into 33 mL oh 1N hydrochloric acid and extracted with ethyl acetate. The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography using 15% ethyl acetate -hexanes as eluant the title compound (1.17 g) was obtained.

후처리

  1. temperatureThe reaction was heated at 58° C. for two hours
  2. customThe cooled reaction
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration, concentration and silica gel column chromatography
  7. customwas obtained

출처 및 근거

ORD 기록
ord-833a6e54d2d04733b394359c809d7828
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756388B1

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