Water → HCID 57723644, compound

HRID 1987448Notes

Reaction equation

HRID 1987448 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[Br:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:25])[CH:16]2[Si:21](Cl)([CH3:23])[CH3:22].O>CCOCC>[Br:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:25])[CH:16]2[Si:21]([CH:4]1[CH:3]=[CH:2][CH:1]=[CH:5]1)([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7612CyclopentadieneHCID 57723626HCID 57723626, compoundHCID 178418339Butyllithium

Product 1

HCID 57723644HCID 57723644, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.32 g (20.0 mmol) of freshly distilled cyclopentadiene in 120 ml of ether, 8.00 ml of 2.5 M (20.0 mmol) nBuLi in hexanes was added dropwise, while vigorously stirring, at 0° C. This mixture was stirred for 2 h at room temperature, and then 6.03 g (20.0 mmol) of (4-bromo-2-methyl-1H-inden-1-yl)(chloro)dimethylsilane was added dropwise over 30 min at −80° C. The resulting mixture was stirred for 1 h at this temperature, for 12 h at room temperature, and then 100 ml of water was added. The organic layer was separated. The aqueous layer was extracted with 2×100 ml of dichlorodimethylsilane. The combined organic fractions were dried over Na2SO4 and evaporated to dryness. The product was isolated using flash-chromatography on Silica Gel 60 (40-63 um, d 30 mm, 1 300 mm, eluent: hexanes). Yield 5.50 g (83%) of colorless oil of a mixture of isomers I, II, and III.

Workup

  1. stirringThis mixture was stirred for 2 h at room temperature
  2. stirringThe resulting mixture was stirred for 1 h at this temperature, for 12 h at room temperature
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with 2×100 ml of dichlorodimethylsilane
  5. dry with materialThe combined organic fractions were dried over Na2SO4
  6. customevaporated to dryness
  7. customThe product was isolated

Sources & evidence

ORD record
ord-5d0f54a4bcac4b919f9b45f8c2bb745a
Source dataset
uspto-grants-2009_06
Patent number
US07550544B2

Reaction notes

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