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

HRID 1798082ノート

反応式

HRID 1798082 の反応式
[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].[CH2:14]1[CH2:19][O:18][CH:17]=[CH:16][CH2:15]1>ClCCl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:19][O:18]2)[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5]

参加物

5

反応物 2

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

生成物 1

HCID 582928652-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde収率 87%

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

A solution of 2,4-dihydroxy-6-methoxymethylbenzaldehyde (4.08 g, 22.4 mmol) in dichloromethane (100 mL) was treated with PPTS (100 mg) and DHP (4.06 mL, 44.8 mmol) at room temperature overnight. The reaction was concentrated to dryness. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=3:1) to afford the title compound (5.18 g, 87%). 1H NMR (300 MHz, CD3OD) δ 12.34 (s, 1H), 10.12 (s, 1H), 6.58 (s, 1H), 6.56 (s, 1H), 5.58 (m, 1H), 4.63 (s, 2H), 3.84-3.81 (m, 1H), 3.66-3.62 (m, 1H), 3.40 (s, 3H), 1.95-1.86 (m, 2H), 1.75-1.62 (m, 4H).

後処理

  1. concentrationThe reaction was concentrated to dryness
  2. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-dbf5f27c025d452ca514ccb891a0836f
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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