Pempidine → Butyl hept-2-ynoate

HRID 1859274

반응식

HRID 1859274 반응식
CN1[C:7](C)(C)[CH2:6][CH2:5][CH2:4][C:3]1(C)[CH3:10].C#CCCCC.Cl[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20]>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:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:20])[C:10]#[C:3][CH2:4][CH2:5][CH2:6][CH3:7]

참가 물질

7

반응물 3

HCID 6603PempidineHCID 127321-HexyneHCID 61140Butyl chloroformate

생성물 1

HCID 303087Butyl hept-2-ynoate수율 90%

시약·촉매·용매 3

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

실험 절차

3.25 g (2.75 mmol) of tetrakis(triphenylphosphine)palladium(0) are introduced into 250 ml of dichloromethane in a 500 ml round-bottomed flask under argon. The dark brown solution is stirred at room temperature for 1 h. Then 150 mg (1.25 mmol) of 4-dimethylaminopyridine, 21.5 g (137.5 mmol) of 1,2,2,6,6-pentamethylpiperidine and 10.25 g (125 mmol) of 1-hexyne are added and heated to reflux at 40° C. Subsequently, 17 g (125 mmol) of n-butyl chloroformate are added dropwise over the course of 60 min. After a reaction time of 24 h, the reaction mixture is worked up by distillation to isolate n-butyl 2-heptynoate in 90% yield.

후처리

  1. temperatureheated
  2. temperatureto reflux at 40° C
  3. distillationAfter a reaction time of 24 h, the reaction mixture is worked up by distillation

출처 및 근거

ORD 기록
ord-2782a910c2a24de28eb54dfbf5de526d
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153786

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