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

HRID 1039110

반응식

HRID 1039110 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d8e640ee29b44a91b2b103197ead0018
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552033B2

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