Dimethyl Sulfide → (E,E)-Farnesyl chloride

온도

0 °C

(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 Merck 9385 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.

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 Merck 9385 silica gel eluted with 3:97 ethyl acetate
12. custompet ether provided 406.5 mg 85%) of a colorless liquid

ORD 기록

ord-aa171c7a5c474f2a804ca7e31808e167

출처 데이터셋

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05212164