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

HRID 519265Notes

Reaction equation

HRID 519265 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). See FIG. 3. 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 103a.

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-b5b4eb6b41034835bfe15e1e9e8ab032
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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