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

HRID 1798038노트

반응식

HRID 1798038 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-cf19c206a4094127922e92424e827f57
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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