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

HRID 844414Notes

Reaction equation

HRID 844414 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). 1H NMR (CDCl3): d0.33 (s, 3 H), 0.38 (s, 3 H), 2.20 (p, 3JHH=7.5 Hz, 2 H), 2.9-3.1 (m, 4 H), 3.84 (s, 1 H), 6.69 (d, 3JHH=2.8 Hz, 1 H), 7.3-7.6 (m, 7 H), 7.68 (d, 3JHH=7.4 Hz, 2 H). 13C NMR (CDCl3): d0.24, 0.38, 26.28, 33.05, 33.18, 46.13, 116.42, 119.71, 127.51, 128.33, 128.64, 129.56, 136.51, 141.31, 141.86, 142.17, 142.41, 144.62. GC-MS: Calculated for C20H21ClSi 324.11, found 324.05.

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-f3e2941eec174632b30aa6ddf48428d0
Source dataset
uspto-grants-2002_04
Patent number
US06380294B1

Reaction notes

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