tert-Butyl (triphenylphosphoranylidene) acetate → Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-

HRID 2202214Notes

Reaction equation

HRID 2202214 reaction equation
O=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.C1(P(=[CH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:32]([O:31][C:29](=[O:30])[CH:28]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1)([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 59834904Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-Yield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-oxocyclobutanecarboxylic acid (0.303 g, 2.66 mmol), tert-butyl triphenylphosphoranylidenacetate (1 g, 2.66 mmol) and toluene (5 mL) was stirred overnight at 90° C. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (solvent gradient; 70→100% ethyl acetate/hexane) to give 3-(2-(tert-butoxy)-2-oxoethylidene)cyclobutanecarboxylic acid (0.500 g, 2.356 mmol, 89%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (solvent gradient; 70→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f47ab6ca16fe47718560830e2ff18abd
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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