Chlorotrimethylsilane → HCID 19801182, compound

HRID 1646602Notes

Reaction equation

HRID 1646602 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][C:20]2=[O:25])[CH:14]=[CH2:15].[CH3:26][Si:27](Cl)([CH3:29])[CH3:28]>O1CCCC1.CCOCC.O>[CH3:26][Si:27]([CH3:29])([CH3:28])[O:25][C:20]1[C:21]2[C:17](=[C:16]([CH2:13][CH:14]=[CH2:15])[CH:24]=[CH:23][CH:22]=2)[CH2:18][CH:19]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 19801174HCID 19801174, compoundHCID 178418339Butyllithium

Product 1

HCID 19801182HCID 19801182, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

1.24 ml of diisopropylamine and 6 ml of tetrahydrofuran are cooled to -40° C., then 4.7 ml of butyllithium is added drop by drop. The temperature is allowed to rise to -20° C., agitation is carried out for 1/4 hour, then 1 g of 4-(2-propenyl)-1-indanone in 10 ml of tetrahydrofuran is introduced at -70° C. After agitation for one hour at -60° C., 1.15 ml of trimethylsilyl chloride in 6 ml of tetrahydrofuran is added, with agitation for one hour at -60° C. The mixture is poured over 100 ml of water and ice and 100 ml of ether. After decanting, the aqueous phase is extracted with ether, the organic phases are reunited, dried and concentrated to dryness without heating, and 1.51 g of expected product is isolated.

Workup

  1. customto rise to -20° C.
  2. waitagitation is carried out for 1/4 hour
  3. customAfter decanting
  4. extractionthe aqueous phase is extracted with ether
  5. customdried
  6. concentrationconcentrated to dryness
  7. temperaturewithout heating

Sources & evidence

ORD record
ord-f3bb77fb21a14bc19754733118689c8c
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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