Hydrochloric Acid → 4,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

HRID 469756ノート

反応式

HRID 469756 の反応式
CO[C:3](=[O:15])[C:4]([CH3:14])([CH3:13])[CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1.[C:16](#[N:18])[CH3:17].[H-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:14][C:4]([CH3:13])([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[C:3](=[O:15])[CH2:17][C:16]#[N:18]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 59253280methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate

生成物 1

HCID 592532944,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (7.67 g, 35.46 mmol) and acetonitrile (2.6 mL, 49.65 mmol) in toluene (20 mL) is added dropwise to the refluxing suspension of 60% sodium hydride in mineral oil (1.99 g, 49.65 mmol) in toluene (40 mL). After the addition, the reaction mixture is stirred at reflux for 3 hours. After this time, the reaction mixture is cooled to room temperature and the aqueous layer is neutralized to PH˜6-7 by adding 1N hydrochloric acid aqueous solution. The layers are combined and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound. It is used without purification.

後処理

  1. additionAfter the addition
  2. temperatureat reflux for 3 hours
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-735c32d3a04f4fc0935e2f002b94f5f1
出典データセット
uspto-grants-2014_01
特許番号
US08629157B2

反応ノート

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