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

HRID 2252921Notes

Reaction equation

HRID 2252921 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-bd428fcb0048411f8053741944374aaf
Source dataset
uspto-grants-2008_01
Patent number
US07323485B2

Reaction notes

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