tert-Butanol → N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

HRID 2376446노트

반응식

HRID 2376446 반응식
[C:1]([OH:5])([CH3:4])([CH3:3])C.[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:19]3[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]([CH3:26])=C(C=C)[C:18]=3[O:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:8])[CH3:7].S([O-])([O-])=[O:37].[Na+].[Na+]>O.C1COCC1>[OH:5][CH:1]([C:4]1[C:18]2[O:17][CH2:16][CH:15]([C:12]3[CH:13]=[CH:14][C:9]([CH:6]([CH3:7])[CH3:8])=[CH:10][CH:11]=3)[C:19]=2[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:32])([CH3:33])[CH3:31])[C:22]=1[CH3:26])[CH2:3][OH:37]

참가 물질

6

반응물 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 23113980N-(3-(4-Isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

생성물 1

HCID 23114170N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide수율 77%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of AD-mix β (4.62 g) in a mixed solvent of water (15 mL), tert-butanol (15 mL) and THF (15 mL) was added with ice-cooling N-(3-(4-isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (670 mg, 1.65 mmol) obtained in Example 83 and the reaction mixture was stirred at 80° C. for 3 hours. To the reaction solution were added water and sodium sulfite and the resulting mixture was stirred at room temperature for 30 minutes. The product was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 558 mg (yield: 77%) of the title compound. Melting point: 159-161° C. (hexane-ethyl acetate).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

출처 및 근거

ORD 기록
ord-d7b63e8492cd431b9fd1eed5befc1fc2
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465815B2

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