Potassium Carbonate → Methyl 3-(benzyloxy)-5-[4-(methanesulfonyl)phenoxy]benzoate

HRID 20491

반응식

HRID 20491 반응식
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].F[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>CN(C=O)C>[C:20]1([CH2:19][O:18][C:16]2[CH:15]=[C:10]([CH:9]=[C:8]([O:7][C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

생성물 1

HCID 53393370Methyl 3-(benzyloxy)-5-[4-(methanesulfonyl)phenoxy]benzoate수율 73.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

Potassium carbonate (3.21 g, 23.2 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in DMF (30 mL) followed by addition of 1-fluoro-4-(methylsulfonyl)benzene (2.02 g, 11.6 mmol) and the reaction was heated at 120° C. for 3 h. The solvent was then removed in vacuo and the residue was taken up in saturated aqueous sodium hydrogencarbonate (50 mL) and ethyl acetate (150 mL). The organic layer was separated, washed with 1M aqueous hydrochloric acid (50 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:4 to 1:1 ethyl acetate:hexanes, afforded the title compound as a colourless oil (3.50 g, 73%).

후처리

  1. customThe solvent was then removed in vacuo
  2. customThe organic layer was separated
  3. washwashed with 1M aqueous hydrochloric acid (50 mL)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography
  8. washeluting with 1:4 to 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-6af20b50dd1745cd86d2fc92c70fc7a5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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