3,4-dihydro-2H-pyran → 2-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran

HRID 1176418

반응식

HRID 1176418 반응식
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

참가 물질

6

반응물 4

HCID 80803,4-dihydro-2H-pyranHCID 1234974-Methyl-3-nitrobenzyl alcoholHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 685034882-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The solution of 9.85 g of 4-methyl-3-nitrobenzyl alcohol in 200 ml of dichloromethane is admixed successively with 10.9 ml of 3,4-dihydro-2H-pyran and 1.12 g of p-toluenesulphonic acid monohydrate. The reaction mixture is stirred at room temperature over 18 hours. The solution is poured onto 1M sodium hydrogencarbonate solution (300 ml) and extracted with tert-butyl methyl ether (2×300 ml). The organic phase is washed with brine (300 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.49 (1:2 EtOAc-heptane); Rt=4.73.

후처리

  1. extractionextracted with tert-butyl methyl ether (2×300 ml)
  2. washThe organic phase is washed with brine (300 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-8f83503703bc45d48aa5817b8b282ad8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

연결된 노트

불러오는 중…