Diethyl dimethylmalonate → HCID 69596330, compound

HRID 2212569Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:11]=[CH:10]2.[CH3:25][CH2:26][O:27][C:28]([C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])=[O:29]>C1COCC1>[CH2:26]([O:27][C:28](=[O:29])[C:30]([CH3:32])([CH3:31])[C:33]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:13]=2)[CH:8]=1)=[O:34])[CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

t-Butyl lithium 1.7 M (99.7 mL, 169.5 mmol) was added slowly to a solution of (6-bromo-naphthalen-2-yloxy)-tert-butyl-dimethyl-silane (26.0 g, 77.1 mmol) in THF (400 mL) cooled to −78° C. under a nitrogen atmosphere. The reaction was stirred at −78° C. for 1 h, and then diethyl dimethyl malonate (43.5 g, 231.2 mmol) was added rapidly. The reaction was stirred an additional 0.5 h, warmed to room temperature, and partitioned between water saturated with KH2PO4 and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated to give 3-[6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl]-2,2-dimethyl-3-oxo-propionic acid ethyl ester as an oil.

Workup

stirringThe reaction was stirred an additional 0.5 h
temperaturewarmed to room temperature
custompartitioned between water saturated with KH2PO4 and ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-2360fe0e9800427aa0fbc36dea6113d8
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102008B2

Reaction notes

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