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

HRID 1919144Notes

Reaction equation

HRID 1919144 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 334a (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 for overnight. After reaction the reaction solution was evaporated in vacuo. The residue was purified by column chromatography eluting with 1:100 ethyl acetate/petroleum ether to give 334b as a yellow oil (6.0 g, 46%). MS: [M+H]+ 227.

Workup

  1. customAfter reaction the reaction solution
  2. customwas evaporated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluting with 1:100 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f1714b8a3f7340a4b2b7d9f3be03affb
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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