Phenol → 2-(2-Fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyran

HRID 911459노트

반응식

HRID 911459 반응식
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[C:4]([F:16])[CH:3]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]Cl.CN1C(=O)CCC1>[F:16][C:4]1[CH:3]=[C:2]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][C:5]=1[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1

참가 물질

7

반응물 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 576563392-(4-Bromo-2-fluorobenzyloxy)-tetrahydropyran

생성물 1

HCID 576563912-(2-Fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyran수율 68%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

Mix under argon atmosphere 2-(4-bromo-2-fluorobenzyloxy)-tetrahydropyran (2.9 g, 10 mmol), phenol (1.9 g, 20 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (184.3 mg, 1.0 mmol), cesium carbonate (6.5 g, 20 mmol) and anhydrous NMP (20 mL). Degas the flask and fill with argon. Add copper(I) chloride (495 mg, 5 mmol) quickly. Degas the flask three times then fill with argon. Heat at 120° C. for 3 h. Cool to ambient temperature. Dilute with EtOAc and filter. Concentrate in vacuo and purify by chromatography on silica gel to obtain the desired intermediate (2.05 g, 68%). MS (ES+) m/z: 325 (M+Na)+.

후처리

  1. customDegas the flask
  2. customDegas the flask three times
  3. temperatureCool to ambient temperature
  4. additionDilute with EtOAc
  5. filtrationfilter
  6. concentrationConcentrate in vacuo
  7. custompurify by chromatography on silica gel

출처 및 근거

ORD 기록
ord-805b42ba7497497e8b021886ea4426ab
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

반응 노트

불러오는 중…