Hydrochloric Acid → Gossyplure

HRID 64597

반응식

HRID 64597 반응식
[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].C([Mg]Cl)CCC.[C:21]([O:24][CH2:25][CH2:26]Br)(=[O:23])[CH3:22].Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH3:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH2:1][CH2:26][CH2:25][O:24][C:21]([CH3:22])=[O:23]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 135641-Acetoxy-2-bromoethaneHCID 54124585Tetradeca-1,5,9-trieneHCID 178418265HCID 178418265, 화합물

생성물 1

HCID 5363265Gossyplure수율 11%

시약·촉매·용매 1

HCID 24193Titanium Tetrachloride촉매

반응 조건

온도
0 °C

실험 절차

1,5,9-Tetradecatriene (10 g, 0.052 mol), n-butylmagnesium chloride (24.8 mL of 2.5M in tetrahydrofuran; 0.062 mol) and titanium tetrachloride (0.52 g, 0.0027 mol) were stirred under an inert atmosphere at about 65° C. for about 4.5 hours. The reaction mixture was then cooled to 0° C. and cuprous bromide (0.14 g, 1.0 mmol) was added. 2-Bromoethyl acetate (6.9 mL, 0.063 mol) was then added dropwise and the mixture allowed to warm slowly to room temperature and stirred for several hours at room temperature. Reaction temperature was then raised to 60° C. for 4 hours before the mixture was cooled, acidified with aqueous HCl, then extracted with hexane. The hexane extract was washed with saturated sodium bicarbonate solution, dried over MgSO4, filtered and solvent removed on the rotary evaporator. GLC analysis of this crude reaction product indicated an 11% yield of gossyplure. It should be recognized that while this reaction represents successful production of gossyplure from 1,5,9 -tetradecatriene in one reaction vessel, the reaction parameters have not been optimized. Consequently, significantly improved yields of gossyplure can be expected upon optimization of various reaction parameters.

후처리

  1. temperatureto warm slowly to room temperature
  2. customReaction temperature
  3. temperaturewas then raised to 60° C. for 4 hours before the mixture
  4. temperaturewas cooled
  5. extractionextracted with hexane
  6. extractionThe hexane extract
  7. washwas washed with saturated sodium bicarbonate solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customsolvent removed on the rotary evaporator
  11. customGLC analysis of this crude reaction product

출처 및 근거

ORD 기록
ord-84f5d1ced4764e9682f1afa69091250d
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609498

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