tert-Butyl acrylate → tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate

HRID 2234182ノート

反応式

HRID 2234182 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:25][CH2:24][C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 728512-(4-Bromophenyl)ethanol

生成物 1

HCID 69136052tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate収率 66.2%

反応条件

温度
0 °C

実験手順

2-(4-Bromophenyl)ethanol (5 g) was treated with benzyltrimethylammonium hydroxide (Triton B®) (0.3 mL) and the resultant mixture was stirred in vacuo for 30 minutes. The mixture was then cooled to 0° C. and treated with t-butyl acrylate (3.5 g). The reaction was warmed to room temperature and stirred for 5 hours. The mixture was filtered through aluminium oxide (15 g) eluting with ether (75 mL). The collected filtrate was concentrated and purified by flash chromatography eluting with ethylacetate:iso-hexane (1:8) to give the sub-titled compound (5.42 g) as an oil.

後処理

  1. temperatureThe reaction was warmed to room temperature
  2. filtrationThe mixture was filtered through aluminium oxide (15 g)
  3. washeluting with ether (75 mL)
  4. concentrationThe collected filtrate was concentrated
  5. custompurified by flash chromatography
  6. washeluting with ethylacetate:iso-hexane (1:8)

出典と根拠

ORDレコード
ord-439c951efb204572a5b85acff77ebe64
出典データセット
uspto-grants-2010_05
特許番号
US07709511B2

反応ノート

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