3,4-dihydro-2H-pyran → 2-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

HRID 1798060노트

반응식

HRID 1798060 반응식
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5]

참가 물질

4

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 582926702,4-Dihydroxy-6-methoxymethyl-benzaldehyde

생성물 1

HCID 582928652-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2,4-dihydroxy-6-methoxymethyl-benzaldehyde (2.62 g, 14.45 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (2.42 g mL, 28.90 mmol) and pyridium p-toluenesulfonic acid (0.050 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 2-hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.06 g, 80%). 1H NMR (400 MHz, CDCl3) δ 12.30 (s, 1H), 10.10 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 5.47 (s, 1H), 4.60 (s, 2H), 3.80 (m, 1H), 3.60 (m, 1H), 3.40 (s, 3H), 2.00-1.50 (m, 6H).

후처리

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

출처 및 근거

ORD 기록
ord-814f564cd6cf40ac8b409e4e16024295
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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