Methyl acetoacetate → HCID 86744710, compound

HRID 1609553Notes

Reaction equation

[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH3:16][C:17]1[C:22](/[CH:23]=[CH:24]/[CH:25]=[O:26])=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:20]=[C:19]([CH3:34])[N:18]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:16][C:17]1[C:22](/[CH:23]=[CH:24]/[CH:25]([OH:26])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[C:21]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[CH:20]=[C:19]([CH3:34])[N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

82.2 μl (0.76 mmol) of methyl acetoacetate are added dropwise at 0° C. under a nitrogen atmosphere to 18.5 mg (0.8 mmol) of sodium hydride in 1 ml of tetrahydrofuran. After 15 minutes, 0.55 ml (0.77 mmol) of n-butyllithium (1.5M in hexane) is added dropwise at 0° C., the mixture is stirred for 15 minutes at 0° C. and 180 mg (0.7 mmol) of the compound from Example 31 are added dropwise in 3 ml of tetrahydrofuran. After 1 h, the mixture is hydrolyzed using saturated ammonium chloride solution and washed three times using dichloromethane, and the organic phases are dried and 0.25 g of oil are obtained after removing the solvent in vacuo.

Workup

waitAfter 1 h
washwashed three times
customthe organic phases are dried

Sources & evidence

ORD record: ord-906bdb58a95643778305e3559d6aa0de
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05401746

Reaction notes

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