Ethyl Acetate → 2-Methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester

HRID 644007노트

반응식

HRID 644007 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:6][C:5]=1[OH:15].Br[CH2:18][C:19]1[CH:38]=[CH:37][C:22]([O:23][CH2:24][C:25]2[N:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:28][C:29]=2[CH3:30])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.CCCCCC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:5]([O:15][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:37][CH:38]=2)=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:8][C:9]=1[CH3:10]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 685799434-(4-Bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazoleHCID 685799482-Hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester

생성물 1

HCID 592632962-Methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

A mixture of the title A compound, 2-hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester (407 mg, 1.81 mmol), the title D compound, 4-(4-bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazole (650 mg, 1.81 mmol) and potassium carbonate (751 mg, 5.44 mmol) in DMF is stirred at RT overnight. The mixture is then partitioned between EtOAc and water. The organic layer is washed with brine, dried with magnesium sulfate and concentrated under vacuum to give the crude product. Chromatography on silica gel, using 10% EtOAc in hexane gives 2-methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester as a white foam: ESI-MS 502 [M+1]+.

후처리

  1. customThe mixture is then partitioned between EtOAc and water
  2. washThe organic layer is washed with brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product

출처 및 근거

ORD 기록
ord-63c4b3974bdc4ebb827541f4c57dc3a4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700637B2

반응 노트

불러오는 중…