Dimethyl Sulfide → (E,E)-Farnesyl chloride

HRID 249127

반응식

HRID 249127 반응식
[Cl:1]N1C(=O)CCC1=O.CSC.[CH3:12]/[C:13](/[CH2:17][CH2:18]/[CH:19]=[C:20](\[CH3:28])/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:27])[CH2:25][CH3:26])=[CH:14]\CO>ClCCl>[Cl:1][CH2:26]/[CH:25]=[C:24](\[CH3:27])/[CH2:23][CH2:22]/[CH:21]=[C:20](\[CH3:28])/[CH2:19][CH2:18][CH:17]=[C:13]([CH3:14])[CH3:12]

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 86746852(E,E)-3,7,11-trimethyl-2,6,10-tridecatrien-1-ol

생성물 1

HCID 6003397(E,E)-Farnesyl chloride수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

(Note: all temperatures indicated are for the contents of the reaction flask). To a stirred solution of 299 mg (2.24 mmol) of N-chlorosuccinimide in 15 ml of dichloromethane at -30° C. under argon was added 0.18 ml (2.45 mmol) of distilled dimethyl sulfide over 5 minutes. After 10 minutes at -30° C., the reaction was allowed to warm to 0° C. for 10 minutes, followed by cooling to -40° C. A solution of 441.4 mg (1.99 mmol) of (E,E)-3,7,11-trimethyl-2,6,10-tridecatrien-1-ol in 5 ml of dichloromethane was added dropwise over 10 minutes. The reaction was allowed to warm gradually to 0° C. over 1 hour, and then maintained at 0° C. for 1 hour. After quenching with cold water, the mixture was extracted with hexane and the hexane extract was washed with cold water and cold brine, dried (MgSO4) and evaporated to afford 483 mg of a crude product. Rapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate:pet ether provided 406.5 mg (85%) of a colorless liquid. 13C NMR indicated that this material contained a trace (3%) impurity.

후처리

  1. temperatureby cooling to -40° C
  2. temperatureto warm gradually to 0° C. over 1 hour
  3. temperaturemaintained at 0° C. for 1 hour
  4. customAfter quenching with cold water
  5. extractionthe mixture was extracted with hexane
  6. extractionthe hexane extract
  7. washwas washed with cold water and cold brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto afford 483 mg of a crude product
  11. washRapid flash chromatography on 20 g of silica gel eluted with 3:97 ethyl acetate

출처 및 근거

ORD 기록
ord-121f6f1bfe7f4a86950d93c1743542f7
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212164

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