Acetone → HCID 18509437, compound

HRID 1356838Notes

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]([CH3:19])[CH:16]=C(Br)[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23]([Li])CCC.CCCCCC.[Cl-].[NH4+].[CH3:36][C:37]([CH3:39])=[O:38]>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:36]([C:37]([OH:38])([CH3:23])[CH3:39])[CH:16]=[C:17]([CH3:19])[CH:18]=2)[CH3:11])=[CH:21][CH:22]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: -75 °C

Procedure

Compound 85 (1.42 g; 3.94 mmol) was dissolved in tetrahydrofuran (20 ml). While the solution was stirred at −75° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.56 M: 2.5 ml; 3.94 mmol) was added dropwise. The mixture was stirred for 15 minutes, and acetone (2 ml) was added dropwise thereto. The resultant mixture was brought to room temperature over 2 hours, and the reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, 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=10:1→4:1), to thereby yield 0.41 g of the target compound as yellow oily matter (yield: 30.6%).

Workup

stirringThe mixture was stirred for 15 minutes
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=10:1→4:1)

Sources & evidence

ORD record: ord-7e417799d17c4062a795195e4bf64655
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586633B1

Reaction notes

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