Acetylene → N-Butyl propiolate

HRID 1859276

反応式

HRID 1859276 の反応式
CN1C(C)(C)CC[CH2:4][C:3]1(C)C.C#C.Cl[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16]>CN(C)C1C=CN=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])[C:3]#[CH:4]

参加物

7

反応物 3

HCID 6326Acetylene3 回HCID 6603PempidineHCID 61140Butyl chloroformate

生成物 1

HCID 11366990N-Butyl propiolate収率 85%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

0.42 g (0.36 mmol) of tetrakis(triphenylphosphine)palladium(0), 20 mg (0.16 mmol) of 4-dimethylamino-pyridine and 2.87 g (18.5 mmol) of 1,2,2,6,6-penta-methylpiperidine are introduced into 30 ml of dichloromethane in a 60 ml autoclave under argon. Then 10 bar of acetylene are injected, and the autoclave is heated to 40° C. 5 g (36.6 mmol) of n-butyl chloroformate are pumped in over the course of 10 min, and then acetylene is further injected to 20 bar. The amount of acetylene taken up is replenished hourly over the course of 24 h, and, after cooling, the reaction discharge is flushed with nitrogen and the reaction mixture is distilled. n-Butyl propiolate is isolated in 85% yield.

後処理

  1. customare pumped in over the course of 10 min
  2. customtaken up is replenished hourly over the course of 24 h
  3. temperatureafter cooling
  4. customthe reaction discharge is flushed with nitrogen
  5. distillationthe reaction mixture is distilled

出典と根拠

ORDレコード
ord-22efaec56935488392cb6fff9daf2f20
出典データセット
uspto-grants-2000_11
特許番号
US06153786

関連ノート

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