Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 23021061, compound

HRID 2223842Notes

Reaction equation

HRID 2223842 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][O:3][CH:2]1O.C1(P(=[CH:32][C:33]([O:35][CH3:36])=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C(O)C.[C].[Pd]>[OH:3][CH2:4][CH2:5][C:6]1([CH2:1][CH2:2][CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester2×HCID 59714835HCID 59714835, compound2×

Product 1

HCID 23021061HCID 23021061, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3oxaspiro[5.5]undecan-2-ol (460 mg) in dichloromethane (15 mL) was added methyl triphenylphosphoranylideneacetate (1.36 g). After stirring the solution under reflux for 3 hours, methyl triphenylphosphoranylideneacetate (1.36 g) was further added thereto. The solution was stirred under reflux for 14 hours. The solution was concentrated under reduced pressure, and the resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1) to give a mixture of an unsaturated ester derivative and 3-oxaspiro[5.5]undecan-2-ol (520 mg) To a solution of the resulting mixture in ethanol (30 mL) was added 10% palladium-carbon (60 mg). The mixture was stirred at room temperature under hydrogen atmosphere for 63 hours. The catalyst was filtered off, concentrated under reduced pressure and the resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1) to give the title compound (210 mg) 1HNMR (CDCl3) δ: 1.23-1.48 (m, 12H), 1.52-1.68 (m, 4H), 2.29 (t, 2H, J=7.2 Hz), 3.62-3.71 (m, 2H), 3.67 (s, 3H).

Workup

  1. temperatureunder reflux for 3 hours
  2. stirringThe solution was stirred
  3. temperatureunder reflux for 14 hours
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1)
  6. customto give
  7. stirringThe mixture was stirred at room temperature under hydrogen atmosphere for 63 hours
  8. filtrationThe catalyst was filtered off
  9. concentrationconcentrated under reduced pressure
  10. customthe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7f2f8b14363d4edf8391559688c53d24
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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