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

HRID 1046439

反応式

HRID 1046439 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-ef3a1fddc06f400a958ecb6933a22cb7
出典データセット
uspto-grants-2013_10
特許番号
US08569302B2

関連ノート

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