3,4-dihydro-2H-pyran → 2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester

HRID 2263393ノート

反応式

HRID 2263393 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11][OH:12])=[O:5])[CH3:2].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[O:9][C:10]=1[CH2:11][O:12][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 592962005-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester

生成物 1

HCID 592961772-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4.8 g 5-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester were dissolved in 75 ml dichloromethane. 1.9 ml 3,4-dihydro-2H-pyran and 870 mg pyridinium p-toluenesulfonate were added and the reaction mixture stirred at room temperature over night. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=3:1=>1:1) to obtain 5.3 g 2-(4-methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=3:1=>1:1)

出典と根拠

ORDレコード
ord-88d21f2682034cb2b48b0806fc4c61a7
出典データセット
uspto-grants-2010_12
特許番号
US07851493B2

反応ノート

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