Hexamethyldisilazane → HCID 18953760, compound

HRID 1492022Notes

Reaction equation

HRID 1492022 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.[Si:15]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)=[O:38])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Si:45]([O:52][CH2:53][CH:54]=[O:55])([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]>O1CCCC1.CCCCCC>[Si:45]([O:52][CH2:53][CH:54]([OH:55])[CH:36]([C:37](=[O:38])[C:39]1[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=1)[CH2:35][CH2:34][CH2:33][O:32][Si:15]([C:28]([CH3:29])([CH3:30])[CH3:31])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:48]([CH3:50])([CH3:51])[CH3:49])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 13838HexamethyldisilazaneHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 18953767HCID 18953767, compoundHCID 178418339Butyllithium

Product 1

HCID 18953760HCID 18953760, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.93 ml (0.0044 mole) of hexamethyldisilazane in 14 ml of tetrahydrofuran, 2.15 ml (0.0044 mole) of 2.06 molar solution of n-butyllithium in hexane is added dropwise with stirring under argon at 0° C. The mixture is cooled to -20° C. and a solution of 1.68 g (0.004 mole) of 5-(t-butyldiphenylsilyloxy)-1-(3-pyridyl)pentan-1-one in 10 ml of tetrahydrofuran is added dropwise over a period of 15 min. The mixture is stirred at -20° C. for 15 min and a solution of 0.74 g (0.0042 mole) of t-butyldimethylsilyloxy acetaldehyde in 15 ml of tetrahydrofurane is added over a period of 1 min. The mixture is stirred at -20° C. for 15 min, quenched with 6 ml of concentrated aqueous ammonium chloride, diluted with ether and washed with water and brine, dried and evaporated. The residue is purified by flash chromatography using ethyl acetate-methylene chloride (1:1) as eluent to give 1-(t-butyldimethylsilyloxy)-6-(t-butyldiphenylsilyloxy)-3-nicotinoylhexan-2-ol described in example 3.

Workup

  1. temperatureThe mixture is cooled to -20° C.
  2. stirringThe mixture is stirred at -20° C. for 15 min
  3. stirringThe mixture is stirred at -20° C. for 15 min
  4. customquenched with 6 ml of concentrated aqueous ammonium chloride
  5. additiondiluted with ether
  6. washwashed with water and brine
  7. customdried
  8. customevaporated
  9. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-cd3855e8afb848cfae82e7c774942cdd
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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