Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetate

HRID 2099689Notes

Reaction equation

HRID 2099689 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][O:13][C:14](=[O:35])[CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14](=[O:35])[CH:15]=[C:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 11063747Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetateYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,4-dioxa-spiro[4.5]decan-8-one (5.00 g, 32.0 mmol) in 65 mL of anhydrous toluene was treated with methyl(triphenylphosphoranylidene)acetate (13.9 g, 41.6 mmol). The mixture was stirred at reflux for 18 h under nitrogen. Solvent was removed and the crude was purified by silica gel column chromatography using a 20% EtOAc:hexanes mixture as eluent to afford (1,4-dioxa-spiro[4.5]dec-8-ylidene)-acetic acid methyl ester (5.51 g, 81%) as a colorless oil.

Workup

  1. temperatureat reflux for 18 h under nitrogen
  2. customSolvent was removed
  3. customthe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8799211966574c398e437c91832f5ee8
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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