Tetrahydrofuran → 2-Fluoro-5-{N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylaminomethyl}phenyl-2-propanol

HRID 1356806노트

반응식

HRID 1356806 반응식
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13](Br)[CH:12]=1)[CH3:9].[CH2:21]([Li])[CH2:22][CH2:23]C.CCCCCC.[Cl-].[NH4+].[O:34]1CCCC1>CC(C)=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:8]([CH2:7][CH:6]=[CH:5][C:4]#[C:3][C:2]([CH3:20])([CH3:19])[CH3:1])[CH3:9])=[CH:12][C:13]=1[CH2:21][CH:22]([OH:34])[CH3:23]

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 18509463trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-4-fluorobenzyl)amineHCID 178418339Butyllithium

생성물 1

HCID 867590562-Fluoro-5-{N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylaminomethyl}phenyl-2-propanol수율 58.5%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
-78 °C

실험 절차

Compound 28 (1.00 g; 2.96 mmol) was dissolved in tetrahydrofuran (15 ml). While the solution was stirred at −78° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.63 M: 1.8 ml; 2.97 mmol) was added dropwise. The mixture was stirred for 10 minutes, and acetone (2 ml) was added dropwise thereto. The mixture was gradually brought to room temperature, and saturated aqueous ammonium chloride solution was added dropwise thereto, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1), to thereby yield 0.55 g of the target compound as yellow oily matter (yield: 58.5%).

후처리

  1. stirringThe mixture was stirred for 10 minutes
  2. customwas gradually brought to room temperature
  3. extractionfollowed by extraction with diethyl ether (100 ml)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1)

출처 및 근거

ORD 기록
ord-924e4240577c4d5ba8b1dbcf9068d64b
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586633B1

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