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

HRID 911459ノート

反応式

HRID 911459 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-805b42ba7497497e8b021886ea4426ab
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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