Dimethyl Sulfoxide → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 129801

반응식

HRID 129801 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([CH3:26])=[CH:13][CH2:14][CH2:15]/[C:16](/[CH3:25])=[CH:17]/[CH2:18][CH2:19]/[C:20](/[CH3:24])=[CH:21]/[CH2:22][OH:23].C(N(CC)CC)C>C(Cl)Cl.C(OCC)C>[CH3:24]/[C:20](/[CH2:19][CH2:18]/[CH:17]=[C:16](\[CH3:25])/[CH2:15][CH2:14][CH:13]=[C:12]([CH3:26])[CH3:11])=[CH:21]\[CH:22]=[O:23]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 445070Farnesol

생성물 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal수율 100.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

To a CH2Cl2 solution (15 mL) of oxalyl chloride (7.81 mL, 87.7 mmol) was added dimethyl sulfoxide (12.5 mL, 175.4 mmol) dropwise over 30 min at -60° C. The resulting clear solution was stirred at this temperature for 20 min. A solution of trans, trans-farnesol (Aldrich Chemical Co.) (15 g, 67.5 mmol) in CH2Cl2 (325 mL) was added dropwise over 15 min. The reaction mixture became cloudy white during addition. The heterogeneous reaction mixture was stirred at -60° C. for 30 min, whereupon triethylamine (56.4 mL, 405 mmol) was added dropwise over 10 min. The reaction mixture became thick. The reaction mixture was allowed to warm to RT over 1 h. Ethyl ether (800 mL) was added and the organic layer was washed with H2O (500 mL), brine (500 mL) and dried over MgSO4. Evaporation gave 15 g (100%) of title compound as a crude oil.

후처리

  1. additionThe reaction mixture became cloudy white during addition
  2. additionwas added dropwise over 10 min
  3. washthe organic layer was washed with H2O (500 mL), brine (500 mL)
  4. dry with materialdried over MgSO4
  5. customEvaporation

출처 및 근거

ORD 기록
ord-afa6e30a1fca4a3ebdbc57adcbef86cc
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

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