3-Phenoxybenzoic acid → 5-Acetyl-4-methyl-2-(3-phenoxyphenyl)oxazole

HRID 128684

反応式

HRID 128684 の反応式
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17](C1C=C(C=CC=1)C(O)=O)[C:18]1[CH:23]=C[CH:21]=[CH:20][CH:19]=1>[OH-].[Na+]>[C:18]([C:19]1[O:12][C:11]([C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)=[N:13][C:20]=1[CH3:21])(=[O:17])[CH3:23]

参加物

4

反応物 2

HCID 195393-Phenoxybenzoic acidHCID 166186253-Phenoxybenzamide

生成物 1

HCID 193749285-Acetyl-4-methyl-2-(3-phenoxyphenyl)oxazole収率 94%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
180 °C

実験手順

A mixture of 3-phenoxybenzamide (2.13 g, 10 mmol), 3-phenoxybenzoic acid (4.28 g, 20 mmol), and 3-chloropenta-2,4-dione (0.44 g, 3.3 mmol) was heated to 180° C. under stirring for 23 h. The hot mixture was poured into 1N aqueous sodium hydroxide (100 ml), and extracted with diethyl ether (100+2×50 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), dried over magnesium sulfate, and evaporated to dryness. Purification by silica gel column chromatography (135 g, 16.7% ethyl acetate in n-hexane) afforded the titled compound as solids in 94% yield: 1H NMR (CDCl3) δ7.88-7.83 (1H, m), 7.77-7.53 (1H, m), 7.49-7.34 (3H, m), 7.18-7.12 (2H, m), 7.07-7.00 (2H, m), 2.55 (3H, s), 2.54 (3 H, s).

後処理

  1. extractionextracted with diethyl ether (100+2×50 ml)
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customPurification by silica gel column chromatography (135 g, 16.7% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-73a8b1f0a08048a8937510601d49b623
出典データセット
uspto-grants-1995_11
特許番号
US05464849

関連ノート

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