Toluene → Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetate

HRID 1190067Notes

Reaction equation

HRID 1190067 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.CC1C([P+]([O:32][C:33]([CH3:35])=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.[C:36]1(C)C=CC=CC=1>>[CH3:36][O:32][C:33](=[O:34])[CH:35]=[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 3

HCID 1140TolueneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 53420851Methyl(triphenylphosphoranylidene) acetate

Product 1

HCID 11063747Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetateYield 81%

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-416fca9b27f045a5bfda00b33c27362f
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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