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

HRID 327895

反応式

HRID 327895 の反応式
[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-]>>[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]

参加物

3

反応物 2

HCID 445070FarnesolHCID 5115033Dimethyl (diazomethyl)phosphonate

生成物 1

HCID 86747432(E,E)-[[(3,7,11-Trimethyl-2,6,10-dodecatrienyl)oxy]methyl]phosphonic acid, dimethyl ester収率 36.4%

実験手順

(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 ##STR87## (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, (36% yield), of the ether as a dark blue/green oil.

後処理

  1. customof dry
  2. customdeoxygenated benzene (10 ml)
  3. additiontreated in one portion with ##STR87## (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

出典と根拠

ORDレコード
ord-67e874669f144f53bde52744efee6c3b
出典データセット
uspto-grants-1993_12
特許番号
US05273969

関連ノート

読み込み中…