Phosphorus oxychloride → Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

HRID 931411

반응식

HRID 931411 반응식
O=P(Cl)(Cl)[Cl:3].[CH3:6][C:7]1[N+:8]([O-])=[C:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12]>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12]

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 68278194Methyl 4-(4,5-Dimethyl-3-oxido-1,3-oxazol-2-yl)benzoate

생성물 1

HCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

POCl3 (2.23 mL, 24.3 mmol) was added dropwise to a stirred solution of N-oxide 1 (5.0 g, 20.2 mmol) in dry DCM (100 mL) and the mixture stirred at 40° C. for 16 h. The solution was poured into a slurry of ice/1 M NaOH solution (100 mL) and the mixture stirred for 10 min. The mixture was extracted with DCM (3×50 mL), the combined organic extract dried and the solvent evaporated. The residue was purified by column chromatography, eluting with 20% EtOAc/pet. ether, to give benzoate 2 (4.12 g, 77%) as a white powder: mp (EtOAc) 127-128° C.; 1H NMR (CDCl3) δ 8.06-8.12 (m, 4H, H-2, H-3, H-5, H-6), 4.56 (s, 2H, CH2Cl), 3.94 (s, 3H, OCH3), 2.45 (s, 3H, CH3); MS m/z 266.6 (MH+, 100%). Anal. calcd for C13H12ClNO3: C, 58.77; H, 4.55; N, 5.27. Found: C, 58.82; H, 4.43; N, 5.18%.

후처리

  1. stirringthe mixture stirred for 10 min
  2. extractionThe mixture was extracted with DCM (3×50 mL)
  3. extractionthe combined organic extract
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with 20% EtOAc/pet. ether

출처 및 근거

ORD 기록
ord-71c5006b86f94a2383682de8def0e8d0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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