반응 #9365

반응 방정식

2-bromo-cyclopent-2-enol

Intermediate D3

2-bromo-cyclopent-2-enol

ethyl vinyl ether

→

1-bromo-5-vinyloxy-cyclopentene

반응 조건

후처리

1. 1
   기타The mixture was quenched with 5% NaOH (150 mL)
2. 2
   여과filtered through celite
3. 3
   농축The residue was concentrated

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 ONE 1) was isolated after flash chromatography on silica gel with hexanes to 5% ethyl acetate:hexanes, 10.4 g (74%).

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