Pyridine → HCID 46945492, 화합물

HRID 2088305

반응식

HRID 2088305 반응식
[CH2:1]([O:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH3:11])[CH2:9][OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C=CC=CC=1.[S:25](Cl)([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl>[S:25]([O:27][CH2:28][CH3:29])([O:10][CH2:9][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:11])=[O:26]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 80784Chlorosulfurous acid, ethyl esterHCID 46945302HCID 46945302, 화합물

생성물 1

HCID 46945492HCID 46945492, 화합물수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

To a solution of alcohol 4 (20.6 g, 79.1 mmol) in CH2Cl2 (200 mL) is added pyridine (8.12 g, 102.8 mmol) and ethyl chlorosulfite (12.2 g, 94.9 mmol). The reaction mixture is stirred at 23° C. for 10 hours. The reaction is quenched with water (100 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic layers are washed with HCl (1N, 100 mL), saturated NaHCO3 (100 mL), brine (100 mL) and dried over anhydrous sodium sulfate. The solvent is removed and the residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane) to give 2,2-bis(hexyloxy)propanyl ethyl sulfite 6 (24.5 g, 88%) as a colorless oil: Rf (15% EtOAc/hexane)=0.44; IR (thin film, cm−1) 2932, 2872, 1467, 1379, 1213, 1194, 1176, 1001, 888; 1H NMR (600 MHz, CDCl3) δ 4.11-4.00 (m, 2H), 3.93 (d, J=10.8 Hz, 1H), 3.77 (d, J=10.8 Hz, 1H), 3.42-3.37 (m, 4H), 1.51-1.48 (m, 4H), 1.33 (s, 3H), 1.31-1.24 (m, 15H), 0.85 (t, J=7.2 Hz, 6H); 13C NMR (150 MHz, CDCl3) δ 99.0, 62.9, 60.8, 58.5, 58.3, 31.6, 29.8, 25.9, 22.6, 20.9, 15.3, 14.0.

후처리

  1. customThe reaction is quenched with water (100 mL)
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. washThe combined organic layers are washed with HCl (1N, 100 mL), saturated NaHCO3 (100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed
  6. customthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-07d5da7df97e4ef7b0d6e464d57fe696
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435756B2

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