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

HRID 2099397Notes

Reaction equation

HRID 2099397 reaction equation
[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

Participants

4

Reactant 2

HCID 8023Ethyl vinyl etherHCID 111374622-Bromo-cyclopent-2-enol2×

Product 1

HCID 219861131-Bromo-5-vinyloxy-cyclopentene

Reagents, catalysts & solvents 1

HCID 16683746DiacetyloxymercuryCatalyst

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-4dfec4a30a9a4583a9e80bb9d270ddc6
Source dataset
uspto-grants-2009_08
Patent number
US07569584B2

Reaction notes

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