Water → (1-{[(3-Phenoxyphenyl)methoxy]methyl}cyclopropyl)methanol

HRID 1194027

反応式

HRID 1194027 の反応式
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[H-].[Na+].[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][CH2:2][C:3]1([CH2:6][O:7][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:18]=2)[CH2:5][CH2:4]1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

生成物 1

HCID 13849406(1-{[(3-Phenoxyphenyl)methoxy]methyl}cyclopropyl)methanol収率 40.5%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 1,1-dihydroxymethylcyclopropane (3 g) in tetrahydrofuran (20 cm3) was added dropwise to a suspension of sodium hydride (0.35 g) in tetrahydrofuran (30 cm3). After effervescence has ceased, tetrabutylammonium iodide (1 g) was added to the grey suspension followed by a solution of 3-phenoxybenzyl bromide (3.88 g) in tetrahydrofuran (15 cm3) at the ambient temperature and the mixture stirred for a further 2 hours. The mixture was poured into water and extracted with ethylacetate. The extracts were combined, dried over magnesium sulphate and concentrated by evaporation of the solvent, and the residual oil purified by column chromatography using a silica gel column eluting first with dichloromethane, followed then by ethylacetate, to give 1-hydroxymethyl-1-(3-phenoxybenzyloxymethyl)cyclopropane (1.7 g).

後処理

  1. extractionextracted with ethylacetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated by evaporation of the solvent
  4. customthe residual oil purified by column chromatography
  5. washeluting first with dichloromethane

出典と根拠

ORDレコード
ord-79fa025abbde4ca799c4dc894185ef47
出典データセット
uspto-grants-1989_03
特許番号
US04812483

関連ノート

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