Dichlorodimethylsilane → HCID 21943898, compound

HRID 2216739Notes

Reaction equation

HRID 2216739 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][C:13]1[CH2:14][C:15]2[C:16]([CH:25]=1)=[C:17]1[C:22](=[CH:23][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18]1.[Li].[Cl:27][Si:28](Cl)([CH3:30])[CH3:29]>CCOCC>[Cl:27][Si:28]([CH:14]1[C:15]2=[CH:24][CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[C:16]2[CH:25]=[C:13]1[CH3:12])([CH3:30])[CH3:29]

Participants

7

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 6020252-Methyl-3H-cyclopenta[a]naphthaleneHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 21943898HCID 21943898, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 1.6 M n-BuLi solution in hexane (7.5 mL, 12 mmol) was added at −50° C. to a solution of 2-methyl-3H-cyclopenta[a]naphthalene (2.14 g, MW=180.25, 11.9 mmol) in 50 mL of ether. The resulting suspension was allowed to warm to room temperature and stirred for 45 min at the same temperature. Then the lithium suspension was cooled again to −70° C. and added of dichlorodimethylsilane (18 mmol, 2.2 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The precipitate of lithium chloride was filtered, the filtrate was evaporated off to dryness and dried in vacuo. Yield 3.14 g (97%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. filtrationThe precipitate of lithium chloride was filtered
  4. customthe filtrate was evaporated off to dryness
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bafd04cec111436c910f86f2a8442160
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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