Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86661240, compound

HRID 1411484Notes

Reaction equation

HRID 1411484 reaction equation
[Cl:1][C:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][C:3]=1[CH:9]=O.[CH2:11]([O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15])[CH3:12]>C1C=CC=CC=1>[Cl:1][C:2]1[CH2:6][C:5]([CH3:7])([CH3:8])[CH2:4][C:3]=1/[CH:9]=[CH:16]/[C:14]([O:13][CH2:11][CH3:12])=[O:15]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 866612412-Chloro-4,4-dimethylcyclopent-1-enecarbaldehyde

Product 1

HCID 86661240HCID 86661240, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The following two procedures were adapted from Organic Preparations and Procedures Int., 29(4):471-498. A 500-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 2-chloro-4,4-dimethylcyclopent-1-enecarbaldehyde (38 g, 240 mmol) in benzene (240 mL). To the solution was added ethoxycarbonylmethylene triphenylphosphorane (84 g, 240 mmol). The mixture was stirred for 14 h. After that time, the solvent was evaporated and the residue was triturated with hexanes (2 L) to extract the product away from the PPh3 by-products. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using a 100% hexane—1:1 hexane/ethyl acetate gradient to afford a 37% yield (20 g) of (E)-ethyl 3-(2-chloro-4,4-dimethylcyclopent-1-enyl)acrylate 107a.

Workup

  1. customA 500-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customAfter that time, the solvent was evaporated
  3. customthe residue was triturated with hexanes (2 L)
  4. extractionto extract the product away from the PPh3 by-products
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8e98c1b7fc1b40e095219220ca8307ca
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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