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

HRID 644007ノート

反応式

HRID 644007 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-63c4b3974bdc4ebb827541f4c57dc3a4
出典データセット
uspto-grants-2010_04
特許番号
US07700637B2

反応ノート

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