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

HRID 2234182노트

반응식

HRID 2234182 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-439c951efb204572a5b85acff77ebe64
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709511B2

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