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

HRID 1194027

반응식

HRID 1194027 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-79fa025abbde4ca799c4dc894185ef47
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04812483

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