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

HRID 1046439

반응식

HRID 1046439 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-ef3a1fddc06f400a958ecb6933a22cb7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569302B2

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