Farnesol → [(3,7,11-Trimethyl-2,6,10-dodecatrienyl)oxymethyl]phosphonic acid, dimethyl ester

HRID 249119

반응식

HRID 249119 반응식
[OH:1][CH2:2]/[CH:3]=[C:4](/[CH2:6][CH2:7]/[CH:8]=[C:9](/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])\[CH3:10])\[CH3:5].[N+](=[CH:19][P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22])=[N-]>CCOCC>[CH3:5][C:4]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3][CH2:2][O:1][CH2:19][P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22]

참가 물질

4

반응물 2

HCID 445070FarnesolHCID 5115033Dimethyl (diazomethyl)phosphonate

생성물 1

HCID 86746850[(3,7,11-Trimethyl-2,6,10-dodecatrienyl)oxymethyl]phosphonic acid, dimethyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

(E,E)-Farnesol, (5.0 mmol, 1.11 g, 1.26 ml) was stirred under argon in 10 ml of dry deoxygenated benzene (10 ml) and treated in one portion with ##STR88## (1.0 mmol, 0.442 g). The dark blue/green solution was stirred at room temperature and a solution of (1.5 g, 10.0 mmol) of dimethyl diazomethylphosphonate (prepared according to D. Seyferth et al, J. Org. Chem., 1971, vol. 36, No. 10, pages 1379 to 1386) in 20 ml of dry, deoxygenated benzene was added dropwise over 4 hours via syringe pump. After addition, the reaction mixture was stirred an additional 45 minutes. The reaction mixture was stripped of solvent and applied as a 75% ethyl acetate/Hexane solution to a flash chromatography column (50 mm diameter, 6" of silica gel) eluted with 75% ethyl acetate/hexane to afford 0.627 g, yield), of the ether as a dark blue/green oil.

후처리

  1. customof dry
  2. customdeoxygenated benzene (10 ml)
  3. additiontreated in one portion with ##STR88## (1.0 mmol, 0.442 g)
  4. custom10, pages 1379 to 1386) in 20 ml of dry
  5. customdeoxygenated benzene
  6. additionwas added dropwise over 4 hours via syringe pump
  7. additionAfter addition
  8. stirringthe reaction mixture was stirred an additional 45 minutes
  9. washeluted with 75% ethyl acetate/hexane
  10. customto afford 0.627 g

출처 및 근거

ORD 기록
ord-ea5ee3c4d18844c79467bb71c60eff5a
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212164

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