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

HRID 1356806Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -78 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-924e4240577c4d5ba8b1dbcf9068d64b
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586633B1

Reaction notes

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