Hexamethyldisilazane → Lithium Hexamethyldisilazide

HRID 1735835Notes

Reaction equation

HRID 1735835 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].C([Li:14])CCC>C1COCC1>[CH3:1][Si:2]([CH3:9])([CH3:8])[N-:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[Li+:14]

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (8 ml) solution of hexamethyldisilazane (615 μl), 1.66 ml of n-butyl lithium (1.56M, hexane solution) was added at -78° C., followed by stirring for 30 minutes to obtain a lithium hexamethyldisilazide solution. To this solution, a THF solution (10 ml) of 1.21 g of (1S,5R,6R,7R)-2-oxa-7-t-butyldimethylsiloxy-6-{(3S)-3-t-butyldimethylsiloxy-1-octynyl}-bicyclo[3.3.0]octan-3-one was dropwise added at -78° C., and the mixture was stirred for 30 minutes. Then, 930 mg of N-fluorobenzenesulfonimide was added thereto at -78° C. The mixture was stirred at -78° C. for 15 minutes, at 0° C. for 30 minutes and at room temperature for 30 minutes, and then poured into a saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:10) to obtain 643 mg of the above-identified compound. 1H-NMR (CDCl3) δ (ppm): 0.04 (m, 12H), 0.88 (m, 21H), 1.0-5.4(m, 16H).

Sources & evidence

ORD record
ord-33910fa2250f47acae9d22f2a90453ca
Source dataset
uspto-grants-1996_07
Patent number
US05538995

Reaction notes

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