Water → 2-(7-Chloroheptyl)-2-cyclopentenone

HRID 426703

반응식

HRID 426703 반응식
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>C(Cl)Cl.CCCCCC>[Cl:36][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 205354882-(7-Hydroxyheptyl)cyclopent-2-en-1-one

생성물 1

HCID 203896822-(7-Chloroheptyl)-2-cyclopentenone

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

The following procedure was adopted from H. Hayaski et al., J. Amer. Chem. Soc., 95, 8749 (1972): To a solution containing 643 mg (3.28 mmol) of 2-(7-hydroxyheptyl)-2-cyclopentenone in 0.47 ml carbon tetrachloride at 35° (temperature of the external water bath), under argon, was added, dropwise over 1 hour, a solution containing 860 mg (3.28 mmol) triphenylphosphine in 3 ml of anhydrous methylene chloride. The yellow solution was stirred for an additional 4.0 hours at ca. 35° and overnight at reflux. The resultant brown residue was taken up in hot hexane and filtered through a sintered glass funnel containing a pad of Celite whereupon the filtrate was reduced in volume and column chromatographed using an 80% silicic acid-20% Celite column and benzene to 80% benzene-20% ethyl acetate in a gradient elution (5 ml fractions). Thus 2-(7-chloroheptyl)-2-cyclopentenone was obtained (20.2 mg) as a pale orange oil.

후처리

  1. additionwas added, dropwise over 1 hour
  2. temperatureat reflux
  3. filtrationfiltered through a sintered glass funnel
  4. additioncontaining a pad of Celite whereupon the filtrate
  5. customchromatographed
  6. washin a gradient elution (5 ml fractions)

출처 및 근거

ORD 기록
ord-19a365b245904985928424d769b46765
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04171331

연결된 노트

불러오는 중…