Tetrahydrofuran → HCID 18509489, compound

HRID 1356852Notes

Reaction equation

[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[C:15](Br)[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23]([Li])[CH2:24][CH2:25]C.CCCCCC.[Cl-].[NH4+].[O:36]1CCCC1>O.CC(C)=O>[Br:19][C:17]1[CH:16]=[C:15]([C:24]([OH:36])([CH3:25])[CH3:23])[CH:14]=[C:13]([CH2:12][N:10]([CH2:9][C:8]2[CH:21]=[CH:22][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=2)[CH3:11])[CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Compound 139 (4.21 g; 9.90 mmol) was dissolved in tetrahydrofuran (40 ml). While the solution was stirred at −78° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.63 M: 6.1 ml; 9.94 mmol) was added dropwise. After 10 minutes, acetone (1.5 ml) was added dropwise thereto, and the mixture was gradually brought to room temperature. Saturated aqueous ammonium chloride solution was added dropwise to the mixture, and water was added 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→2:1), to thereby yield 3.11 g of the target compound as pale yellow oily matter (yield: 77.7%).

Workup

customwas gradually brought to room temperature
additionwas added
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→2:1)

Sources & evidence

ORD record: ord-e382009b95bb448bbfc7d43a7c7479ce
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586633B1

Reaction notes

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