Chlorotrimethylsilane → HCID 68649276, compound

HRID 1724002Notes

Reaction equation

HRID 1724002 reaction equation
N(C(C)C)C(C)C.[Li]CCCC.[Si:13](Cl)([CH3:16])([CH3:15])[CH3:14].[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[O:43])[CH2:30][C:31]3[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=3)[CH:25]=2)[O:20]1>C1COCC1.C(OCC)C>[CH3:18][C:19]1([CH3:44])[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:29]([O:43][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:30][C:31]3[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=3)[CH:25]=2)[O:20]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 9799516HCID 9799516, compoundHCID 178418339Butyllithium

Product 1

HCID 68649276HCID 68649276, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

i-Pr2NH (0.556 mL, 4.04 mmol), distilled from CaH, was added to THF (7 mL) and cooled to −78° C. A solution of n-BuLi (2.59 M in THF, 1.56 mL, 4.04 mmol) was added dropwise. After completion of addition the reaction mixture stirred at −30° C. for 35 minutes and then cooled down again to −78° C. TMS-Cl (0.546 mL) and 1-(2,2-dimethyl-chroman-6-yl)-2-(3,4,5-trimethoxy-phenyl)-ethanone (1.20 g, 3.23 mmol) dissolved in THF (25 mL) were added dropwise to the stirring reaction mixture. After completion of addition the reaction mixture continued stirring at −78° C. for an additional 30 minutes before being warmed up to −30° C. After stirring at −30° C. for 1 hour the reaction was diluted with diethyl ether and warmed to room temperature. At room temperature the reaction mixture was concentrated and the resulting crude material was purified using silica gel chromatography (4:1 pentane: ethyl acetate to 1:1 pentane: ethyl acetate) to obtain the desired compound (879.1 mg, 74% yield based on recovered starting material).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. temperaturecooled down again to −78° C
  3. additionwere added dropwise to the stirring reaction mixture
  4. additionAfter completion of addition the reaction mixture
  5. stirringcontinued stirring at −78° C. for an additional 30 minutes
  6. temperaturebefore being warmed up to −30° C
  7. stirringAfter stirring at −30° C. for 1 hour the reaction
  8. temperaturewarmed to room temperature
  9. concentrationAt room temperature the reaction mixture was concentrated
  10. customthe resulting crude material was purified

Sources & evidence

ORD record
ord-060715dd5e044a1390315db3a213d6e3
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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