Ethyl orthoformate → Methyl benzo[d]oxazole-7-carboxylate

HRID 380521

反応式

HRID 380521 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](O)[C:5]=1N.C(OC([O:20][CH2:21]C)OCC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+:34]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:20][CH:21]=[N:34][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:12]

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 205248Anthranilic acid, 3-hydroxy-, methyl esterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 19771047Methyl benzo[d]oxazole-7-carboxylate収率 477.6%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A solution of 0.22 g (1.32 mmol) of methyl-2-amino-3-hydroxybenzoate, 0.77 mL (4.6 mmol) of triethylorthoformate and 0.066 g (0.26 mmol) of pyridinium p-toluene sulfonate in 15 mL of xylene was heated at reflux for 18 h. The reaction mixture was concentrated and purified by chromatograph (silica, hexanes:EtOAc, 6:1) to give 0.22 g of the title compound.

後処理

  1. temperatureat reflux for 18 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by chromatograph (silica, hexanes:EtOAc, 6:1)

出典と根拠

ORDレコード
ord-2cb093ad0c064a02b678eded3a8a4b5c
出典データセット
uspto-grants-2001_10
特許番号
US06303593B1

関連ノート

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