Tetrahydrofuran → HCID 10341205, 화합물

HRID 349725노트

반응식

HRID 349725 반응식
[Mg].[Cl:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[O:10][CH3:11].[Si](O[CH:20]1[CH2:24][C:23](=[O:25])[C:22]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)=[CH:21]1)(C(C)(C)C)(C)C.[O:38]1CCCC1>>[OH:38][CH:24]1[C:23](=[O:25])[C:22]([C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=2)=[C:21]([C:7]2[CH:6]=[CH:5][C:4]([O:10][CH3:11])=[C:3]([Cl:2])[CH:8]=2)[CH2:20]1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 30165374-Bromo-2-chloroanisoleHCID 5462224MagnesiumHCID 69110186HCID 69110186, 화합물

생성물 1

HCID 10341205HCID 10341205, 화합물

실험 절차

A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3×35 ml), washed with water (2×20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A)

후처리

  1. customReaction
  2. customwas then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran
  3. customwas removed under reduced pressure
  4. customthe residual reaction mixture
  5. extractionwas extracted with ethyl acetate (3×35 ml)
  6. washwashed with water (2×20 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether)

출처 및 근거

ORD 기록
ord-a9576572c5124dd0afedcff1b018c3f3
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179937B2

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