Cesium carbonate → 1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester

HRID 1039110

反応式

HRID 1039110 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1)=[O:19]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

生成物 1

HCID 688451721-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 3.26 g caesium carbonate and 1.01 g methyl 1-hydroxy-2-naphthoate in 10 ml abs. DMF was added 1.21 g 1-bromomethyl-4-trifluoromethyl-benzene and the mixture was reacted for 3 h at room temperature. The reaction was partitioned between water and ethyl acetate and the aqueous layer was extracted with ethyl acetate twice. The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The resulting residue was purified by chromatography (silica, heptane) to yield 1.62 g of 1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester.

後処理

  1. customthe mixture was reacted for 3 h at room temperature
  2. customThe reaction was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by chromatography (silica, heptane)

出典と根拠

ORDレコード
ord-d8e640ee29b44a91b2b103197ead0018
出典データセット
uspto-grants-2013_10
特許番号
US08552033B2

関連ノート

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