Water → HCID 69025373, compound

HRID 1866796Notes

Reaction equation

HRID 1866796 reaction equation
Br[C:2]1[C:6](OC)([CH3:7])[CH2:5][CH2:4][C:3]=1[CH3:10].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[Si:16]([CH3:20])([CH3:19])(Cl)Cl.O.[CH2:22](OCC)C>C(OC(=O)C)C>[CH3:10][C:3]1[CH2:4][CH:5]=[C:6]([CH3:7])[C:2]=1[Si:16]([C:14]1[CH:22]=[CH:11][CH2:12][CH:13]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 6398DichlorodimethylsilaneHCID 11435662HCID 11435662, compoundHCID 178418339Butyllithium

Product 1

HCID 69025373HCID 69025373, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

2-bromo-3-methoxy-1,3-dimethyl-cyclopentene (5 g, 24.38 mmol) was dissolved in 30 ml of diethylether and the reactant solution was cooled to −30° C. using a Schlenk line in a nitrogen atmosphere. Then, n-butyllithium (6.67 g) was added and the resultant solution was incubated at an elevated temperature for 15 minutes until a white solid was obtained and then again cooled to −30° C. 1 eq. (3.14 g) of Me2SiCl2 was added and the resultant solution was incubated for 5 hours while gradually being heated to room temperature. Then, NaCp (12.5 ml, 25.0 mmol, 2M in THF) was added to the first reactor preset to −30° C. and the resultant solution was incubated at room temperature for 5 hours or more. 20 ml of water and 20 ml of ethylacetate were added thereto and an aqueous layer was once Washed with 20 ml of ethylacetate and then stirred with 50 ml of 1 N HCl for 3 minutes. The resultant solution was neutralized with 50 ml of a saturated sodium bicarbonate solution, and subjected to solvent removal in a rotary evaporator and then to water removal using magnesium sulfate. Finally, the residue was purified by silica-based column chromatography (hexane), to give (2,5-dimethyl-cyclopenta-1,4-dienyl)(cyclopenta-1,4-dienyl)-dimethylsilane (yield: 66%).

Workup

  1. customwas obtained
  2. temperatureagain cooled to −30° C
  3. temperaturewhile gradually being heated to room temperature
  4. washan aqueous layer was once Washed with 20 ml of ethylacetate
  5. customsubjected to solvent removal in a rotary evaporator
  6. customto water removal
  7. customFinally, the residue was purified by silica-

Sources & evidence

ORD record
ord-5829ce90454e48ec99a494feef7d3c0e
Source dataset
uspto-grants-2009_12
Patent number
US07629481B2

Reaction notes

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