Dichlorodimethylsilane → Chlorodimethyl(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silane

HRID 369438Notes

Reaction equation

HRID 369438 reaction equation
[C:1]1([C:7]2[C:18]3[CH:17]=[C:16]4[C:12]([CH2:13][CH2:14][CH2:15]4)=[CH:11][C:10]=3[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][Li].[Si:21]([CH3:25])([CH3:24])(Cl)[Cl:22]>C1COCC1>[Cl:22][Si:21]([CH3:25])([CH3:24])[CH:9]1[C:10]2[C:18](=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][C:12]=3[CH:11]=2)[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8]1

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 139759Lithium, mol. (Li2)HCID 186283771,2,3,5-Tetrahydro-7-phenyl-s-indacene

Product 1

HCID 18628376Chlorodimethyl(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silaneYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,2,3,5-Tetrahydro-7-phenyl-s-indacene, dilithium salt (12.2075 g, 0.05102 moles) in THF (50 mL) was added dropwise to a solution of Me2SiCl2 (19.5010 g, 0.1511 moles) in THF (100 mL) at 0° C. This mixture was then allowed to stir at room temperature overnight. After the reaction period the volatiles were removed and the residue extracted and filtered using hexane. The removal of the hexane resulted in the isolation of the desired product as a yellow oil (15.1492 g, 91.1% yield).

Workup

  1. customAfter the reaction period the volatiles
  2. customwere removed
  3. extractionthe residue extracted
  4. filtrationfiltered
  5. customThe removal of the hexane

Sources & evidence

ORD record
ord-871633eb13074c5897b1fd0c68809fda
Source dataset
uspto-grants-2000_10
Patent number
US06136923

Reaction notes

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