Acetylene → N-Butyl propiolate

HRID 1859276

반응식

HRID 1859276 반응식
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]

참가 물질

7

반응물 3

HCID 6326Acetylene3회HCID 6603PempidineHCID 61140Butyl chloroformate

생성물 1

HCID 11366990N-Butyl propiolate수율 85%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22efaec56935488392cb6fff9daf2f20
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153786

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