Potassium Carbonate → 3-(2,2-Dimethyl-but-3-ynyloxy)-tetrahydro-furan

HRID 1046445Notes

Reaction equation

HRID 1046445 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[CH3:13][C:14]([CH3:24])([CH2:17][O:18][CH:19]1[CH2:23][CH2:22][O:21][CH2:20]1)[CH:15]=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:13][C:14]([CH3:24])([C:15]#[CH:1])[CH2:17][O:18][CH:19]1[CH2:23][CH2:22][O:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 581140682,2-Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 581138943-(2,2-Dimethyl-but-3-ynyloxy)-tetrahydro-furanYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (418 mg, 2.17 mmol) was added to a stirred suspension of 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propionaldehyde (250 mg, 1.45 mmol) and K2CO3 (601 mg, 4.35 mmol) in methanol (17.0 mL) at room temperature. After overnight stirring the bulk of the methanol was removed by rotary evaporation and the reaction mixture partitioned between ethyl ether and NaHCO3. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to provide a crude liquid. Purification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes followed by bulb to bulb distillation under reduced pressure provided 3-(2,2-dimethyl-but-3-ynyloxy)-tetrahydro-furan (169 mg, 69%) as a colorless liquid.

Workup

  1. customwas removed by rotary evaporation
  2. customthe reaction mixture partitioned between ethyl ether and NaHCO3
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto provide a crude liquid
  8. customPurification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes
  9. distillationfollowed by bulb to bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-98354c45ae644b1c8ee0ef5e70b1982b
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

Loading…