3,4-dihydro-2H-pyran → Methyl 3-(oxan-2-yloxy)propanoate

HRID 1749685

반응식

HRID 1749685 반응식
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 80252Propanoic acid, 3-hydroxy-, methyl ester

생성물 1

HCID 15614101Methyl 3-(oxan-2-yloxy)propanoate수율 59.1%

시약·촉매·용매 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)촉매HCID 6344Dichloromethane용매

실험 절차

Pyridinium p-toluenesulfonate (7.65 g, 30.45 mmol) was added to a clear solution of methyl 3-hydroxypropanoate (63.4 g, 609.00 mmol) and 3,4-dihydro-2H-pyran (78 mL, 852.60 mmol) in dichloromethane (650 mL) at room temperature under nitrogen to give a cloudy solution. This was allowed to stir at room temperature overnight. The reaction mixture was washed with water (250 mL) and brine (250 mL) before drying (MgSO4) and evaporating to an oil. This crude product was purified by flash silica chromatography, elution gradient 15 to 30% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate (67.7 g, 59.0%) as a colourless oil: 1H NMR Spectrum: (CDCl3) 1.47 (4H, dddd), 1.55-1.84 (2H, m), 2.55 (2H, t), 3.33-3.53 (1H, m), 3.53-3.7 (4H, m), 3.78 (1H, ddd), 3.93 (1H, dt), 4.42-4.72 (1H, m); Mass Spectrum [MH]+=189.

후처리

  1. customto give a cloudy solution
  2. washThe reaction mixture was washed with water (250 mL) and brine (250 mL)
  3. dry with materialbefore drying (MgSO4)
  4. customevaporating to an oil
  5. customThis crude product was purified by flash silica chromatography, elution gradient 15 to 30% EtOAc in heptane
  6. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-5257f926bd704cdaad71642236d2430f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156831B2

연결된 노트

불러오는 중…