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

HRID 128684

반응식

HRID 128684 반응식
[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]

참가 물질

4

반응물 2

HCID 195393-Phenoxybenzoic acidHCID 166186253-Phenoxybenzamide

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
180 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-73a8b1f0a08048a8937510601d49b623
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464849

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