Boron trifluoride → HCID 20522869, 화합물

HRID 223240노트

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HRID 223240 반응식
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19](O)C)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].B(F)(F)F.[N+]([CH3:29])([O-])=O>C(Cl)Cl>[CH3:18][O:17][C:16]1[CH:15]=[C:14]2[C:4](=[CH:12][C:11]=1[O:10][CH3:9])[C:2]([CH3:29])([C:1]([O:6][CH2:7][CH3:8])=[O:5])[O:3][CH2:19][CH2:13]2

참가 물질

6

반응물 4

HCID 6356Boron trifluorideHCID 6375NitromethaneHCID 12041Ethyl pyruvateHCID 4364381-(3,4-Dimethoxyphenyl)ethanol

생성물 1

HCID 20522869HCID 20522869, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl pyruvate (1.00 g, 0.0086 m), 3,4-dimethoxyphenylethanol (1.57 g, 0.0086 m), and, 1 ml of BF3 etherate are stirred at 25° C. in 20 ml of nitromethane for 45 minutes. The mixture is dissolved in methylene chloride and extracted with aqueous sodium bicarbonate. The organic phase is dried (sodium sulfate), concentrated, and chromatographed on silica gel to give 1.4 g of 6,7-dimethoxy-1-methyl-1-carboethoxyisochroman. A 0.5 g sample of this is dissolved in ether and treated with 100 mg of LAH. After 10 minutes, the mixture is quenched with ethyl acetate and partitioned between 1 N aqueous sodium hydroxide and CH2Cl2. The organic phase yields 0.34 g of 6,7-dimethoxy-1-methyl-1-hydroxymethylisochroman. This is dissolved in THF and treated sequentially with sodium hydride and then o-tetrahydropyranyl chloroethanol. The adduct, upon treatment with acid and water, yields 2-[(7,8-dimethoxy-1-methyl-isochroman-1-yl)methoxy]ethanol. In the manner of Preparation 7, this can be converted to its benzenesulfonates ##STR21## Furthermore, 2-[(1-methylisochroman-1-yl)methoxy]ethanols, with various substituents on the isochroman ring, can be prepared by using the appropriate phenyl ethanols whose substituents, R1 -R5 (vide supra), are analogous to those substituents of the isochromans of Table 3.

후처리

  1. extractionextracted with aqueous sodium bicarbonate
  2. dry with materialThe organic phase is dried (sodium sulfate)
  3. concentrationconcentrated
  4. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-084b9e730e094b9fa8e953769e81f6ce
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04352805

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