Cesium carbonate → 3-((3-Bromophenoxy)methyl)pentan-3-ol

HRID 74338ノート

反応式

HRID 74338 の反応式
[CH2:1]([C:3]1([CH2:6][CH3:7])[CH2:5][O:4]1)[CH3:2].[Br:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:5][C:3]([OH:4])([CH2:6][CH3:7])[CH2:1][CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 2959712,2-Diethyloxirane

生成物 1

HCID 673170023-((3-Bromophenoxy)methyl)pentan-3-ol

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

2,2-Diethyloxirane (6.5 g of a 60% crude, 40 mmol), 3-bromophenol (5.7 g, 33 mmol), and cesium carbonate (12.0 g, 37 mmol) were combined in anhydrous DMSO (20 mL) in a sealed pressure tube and the reaction was stirred and heated at 120° C. for 2 d. Crude product was extracted from water with diethyl ether. The combined organic was washed with brine, dried over Na2SO4, filtered and concentrated under reduced vacuum. Purification by flash chromatography (0-20% EtOAc/hexanes gradient) gave 3-((3-bromophenoxy)methyl)pentan-3-ol as a colorless oil. Yield (7.1 g, 79%): NMR (400 MHz, CDCl3) δ 7.19 (t, J=8.0 Hz, 1H), 7.05-7.12 (m, 2H), 6.90-6.94 (m, 1H), 4.31 (s, 1H), 3.71 (s, 2H), 1.41-1.55 (m, 4H), 0.80 (t, J=7.6 Hz, 6H).

後処理

  1. extractionCrude product was extracted from water with diethyl ether
  2. washThe combined organic was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced vacuum
  6. customPurification by flash chromatography (0-20% EtOAc/hexanes gradient)

出典と根拠

ORDレコード
ord-7efadc1324c640deab996a67ddde556b
出典データセット
uspto-grants-2014_09
特許番号
US08829244B2

反応ノート

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