Dichloromethane → HCID 57386254, compound

HRID 2406858Notes

Reaction equation

HRID 2406858 reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][C@H:7]([CH:13]=C)[CH2:8][CH2:9][C:10]#[C:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[CH2:17](Cl)Cl>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[C:1]([Si:5]([O:6][C@H:7]1[CH2:8][CH2:9][C:10]([C:11]([CH3:12])=[CH2:17])=[CH:13]1)([CH3:15])[CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86661510HCID 86661510, compound

Product 1

HCID 57386254HCID 57386254, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 178479819HCID 178479819, compoundCatalyst

Conditions

Temperature
-78 °C

Procedure

A solution of compound (5a) (263.8 mg, 1.106 mmol) and degassed DCM (37) was cooled to −78° C. The flask was flushed with ethylene gas over a period of 10 minutes before ethylene gas was bubbled through the solution itself for 3 additional minutes. Grubbs I catalyst (136.4 mg, 0.1657 mmol) was added and once again ethylene gas was bubbled through the resulting mixture for one minute. The icebath was removed and the mixture stirred for 24 hours. The flask was flushed with argon and the solvent was evaporated. Chromatography of the residue (pentane/ether 200/1) furnished 226.6 mg of compound of (6a) as clear colourless oil with 86% yield.

Workup

  1. customThe flask was flushed with ethylene gas over a period of 10 minutes before ethylene gas
  2. customwas bubbled through the solution itself for 3 additional minutes
  3. customonce again ethylene gas was bubbled through the resulting mixture for one minute
  4. customThe icebath was removed
  5. customThe flask was flushed with argon
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3bc1312c4127483d924f91bc20d389cb
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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