3,4-dihydro-2H-pyran → methyl 4-(2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-oxobutanoate

HRID 1798038ノート

反応式

HRID 1798038 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]([C:8]1[C:13](C)=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[OH:16])=[O:7].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>ClCCl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:15][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:18]2)=[CH:10][C:9]=1[OH:16])=[O:7]

参加物

4

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 582926554-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

生成物 1

HCID 59525512methyl 4-(2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-oxobutanoate収率 84.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-(2,4-dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (1.0 g, 4.20 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (0.38 mL, 8.40 mmol) and pyridium p-toluenesulfonic acid (0.010 g) at room temperature. The resulting mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 4-[2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-butyric acid methyl ester (1.1 g, 81%). 1HNMR (400 MHz, CDCl3): 12.40 (s, 1H), 6.95 (s, 1H), 6.90 (s, 1H), 5.90 (br s, 1H), 3.27 (t, J=7.8 Hz, 2H), 2.78 (t, J=7.8 Hz, 2H), 2.30 (s, 3H).

後処理

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-cf19c206a4094127922e92424e827f57
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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