Acetone → HCID 18509448, compound

HRID 1356794Notes

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]=[C:15]([CH3:17])[CH:14]=C(Br)[CH:12]=1)[CH3:9].[CH2:21]([Li])CCC.CCCCCC.[Cl-].[NH4+].[CH3:34][C:35]([CH3:37])=[O:36]>O1CCCC1>[CH3:1][C:2]([CH3:19])([CH3:20])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:34]([C:35]([OH:36])([CH3:21])[CH3:37])[CH:14]=[C:15]([CH3:17])[CH:16]=1)[CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

Compound 16 (2.24 g; 6.70 mmol) was dissolved in tetrahydrofuran (25 ml), and the solution was cooled to −78° C. under nitrogen atmosphere. n-butyl lithium in n-hexane (1.56 M: 4.3 ml; 6.70 mmol) was added dropwise to the resultant mixture, and stirred for 15 minutes. Acetone (3 ml) was added dropwise to the mixture, and brought to room temperature over 3 hours, followed by stirring for 1 hour at room temperature. Reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether (50 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), to thereby yield 1.13 g of the target compound (yield: 53.8%).

Workup

waitbrought to room temperature over 3 hours
stirringby stirring for 1 hour at room temperature
customReaction
extractionfollowed by extraction with diethyl ether (50 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)

Sources & evidence

ORD record: ord-220f698f75b248a891fd18cfba48ca6d
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586633B1

Reaction notes

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