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

HRID 1046439Notes

Reaction equation

HRID 1046439 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[CH3:13][C:14]([CH3:25])([CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[CH:15]=O.C([O-])([O-])=O.[K+].[K+]>CO.C(OCC)C>[CH3:13][C:14]([CH3:25])([C:15]#[CH:1])[CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 132764582,2-Dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)propanalHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 581139252-(2,2-Dimethyl-but-3-ynyloxy)-tetrahydro-pyranYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (486 mg, 2.54 mmol) was added to a stirred suspension of 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propionaldehyde (315 mg, 1.69 mmol) and K2CO3 (700 mg, 5.07 mmol) in methanol (20.0 mL) at room temperature. After overnight stirring, the reaction was diluted with diethyl ether, washed with sat. NaHCO3, brine, dried over Na2SO4 and concentrated to provide a crude oil. Purification by flash column chromatography on silica gel using 20% ethyl ether in hexanes provided 2-(2,2-dimethyl-but-3-ynyloxy)-tetrahydro-pyran (147 mg, 48%) as a pale liquid.

Workup

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto provide a crude oil
  5. customPurification by flash column chromatography on silica gel using 20% ethyl ether in hexanes

Sources & evidence

ORD record
ord-ef3a1fddc06f400a958ecb6933a22cb7
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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