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

HRID 1749685

反応式

HRID 1749685 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5257f926bd704cdaad71642236d2430f
出典データセット
uspto-grants-2015_10
特許番号
US09156831B2

関連ノート

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