Tetrahydrofuran → HCID 10341205、化合物

HRID 349725

反応式

HRID 349725 の反応式
[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

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 30165374-Bromo-2-chloroanisoleHCID 5462224MagnesiumHCID 69110186HCID 69110186、化合物

生成物 1

HCID 10341205HCID 10341205、化合物

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-a9576572c5124dd0afedcff1b018c3f3
出典データセット
uspto-grants-2007_02
特許番号
US07179937B2

関連ノート

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