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

HRID 1636217Notes

Reaction equation

HRID 1636217 reaction equation
[C:1]1([C:7]2[C:18]3[CH:17]=[C:16]4[C:12]([CH2:13][CH2:14][CH:15]4[Li])=[CH:11][C:10]=3C[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:20]([CH3:24])([CH3:23])([Cl:22])Cl.[CH2:25]1COCC1>>[Cl:22][Si:20]([CH3:24])([CH3:25])[CH:23]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:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8]1

Participants

4

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 8028Tetrahydrofuran2×HCID 178506813HCID 178506813, compound

Product 1

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

Conditions

Temperature
22.5 °C

Procedure

(7-phenyl-1,2,3,5-tetrahydro-s-indacenyl)lithium (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 20-25° C. for 16 hours. 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 percent).

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-b11f7dcd40b54f74b96f3107d9daf49b
Source dataset
uspto-grants-2000_03
Patent number
US06034022

Reaction notes

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