Ethyl vinyl ether → 1-Bromo-5-vinyloxy-cyclopentene

HRID 656180

반응식

HRID 656180 반응식
[Br:1][C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1.[CH:8](OCC)=[CH2:9]>[Hg](OC(C)=O)OC(C)=O>[Br:1][C:2]1[CH:3]([O:7][CH:8]=[CH2:9])[CH2:4][CH2:5][CH:6]=1

참가 물질

4

반응물 2

HCID 8023Ethyl vinyl etherHCID 111374622-Bromo-cyclopent-2-enol2회

생성물 1

HCID 219861131-Bromo-5-vinyloxy-cyclopentene

시약·촉매·용매 1

HCID 16683746Diacetyloxymercury촉매

실험 절차

A solution of 2-bromo-cyclopent-2-enol (Intermediate D3) (21.7 g, 133.1 mmol) in ethyl vinyl ether (300 mL) was treated with Hg(OAc)2 (31.8 g, 99 mmol) at rt for 60 h. The mixture was quenched with 5% NaOH (150 mL) and filtered through celite. The residue was concentrated to yield 1-bromo-5-vinyloxy-cyclopentene as a pale yellow oil, 14.2 g (46%). 1-Bromo-5-vinyloxy-cyclopentene (14.1 g, 74.4 mmol) in toluene was heated in a re-sealable tube at 130° C. for 24 h. (2-Bromo-cyclopent-2-enyl)-acetaldehyde (Intermediate ONE1) was isolated after flash chromatography on silica gel with hexanes to 5% ethyl acetate:hexanes, 10.4 g (74%).

후처리

  1. customThe mixture was quenched with 5% NaOH (150 mL)
  2. filtrationfiltered through celite
  3. concentrationThe residue was concentrated

출처 및 근거

ORD 기록
ord-35f7b0e0b7f94c74ad549dfb6565b472
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071635B2

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