Hydrochloric Acid → 5-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrile

HRID 2069117ノート

反応式

HRID 2069117 の反応式
[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15]C)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19](#[N:21])[CH3:20].Cl>C1(C)C=CC=CC=1>[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13](=[O:15])[CH2:20][C:19]#[N:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

生成物 1

HCID 585647415-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrile収率 120.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a suspension of sodium hydride (1.62 g of a 60% w/w dispersion in mineral oil, 40.5 mmol) in toluene (20 mL) at reflux was added a solution of methyl 3-(benzyloxy)-2,2-dimethylpropanoate [Eur. J. Org. Chem., 2007 (6) 934-942] (6.00 g, 27.0 mmol) and acetonitrile (2.12 ml, 40.5 mmol) in toluene, dropwise over 1 hr. The reaction mixture was heated for a further 5 hr at reflux then cooled to RT. The mixture was acidified to pH 4 with aqueous hydrochloric acid (1M) and extracted with EtOAc. The organic extract was washed with water and with brine then dried (MgSO4) and evaporated in vacuo to afford 5-(benzyloxy)-4,4-dimethyl-3-oxopentanenitrile as a yellow oil (7.50 g, 96%): m/z 232 (M+H)+ (ES+), which was used without purification in the next step.

後処理

  1. temperatureat reflux
  2. temperatureThe reaction mixture was heated for a further 5 hr
  3. temperatureat reflux
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water and with brine
  7. dry with materialthen dried (MgSO4)
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-ff11871b1c184625be27e8a958e2814e
出典データセット
uspto-grants-2012_10
特許番号
US08299074B2

反応ノート

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