Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-Ethyl 3-(3-Chlorobicyclo[2.2.1]hept-2-en-2-yl)acrylate

HRID 592730Notes

Reaction equation

HRID 592730 reaction equation
[Cl:1][C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[C:3]=1[CH:9]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[C:3]=1/[CH:9]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 580440113-Chlorobicyclo[2.2.1]hept-2-ene-2-carbaldehyde

Product 1

HCID 58043644(E)-Ethyl 3-(3-Chlorobicyclo[2.2.1]hept-2-en-2-yl)acrylateYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 167a (9.0 g, 57.7 mmol) in methylene chloride (250 mL) was added ethyl 2-(triphenyl-λ5-phosphanylidene)acetate (20 g, 57.7 mmol). The mixture was stirred at room temperature overnight. It was then evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:100 ethyl acetate/petroleum ether to afford 167b as a yellow oil (6.0 g, 46%). MS: [M+H]+ 227.

Workup

  1. customIt was then evaporated under reduced pressure
  2. customThe residue was purified by silica-gel column chromatography
  3. washeluting with 1:100 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-82aa937b53f44a08a6f946849190585b
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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