HCID 58348421, compound → HCID 58348350, compound

HRID 2192322Notes

Reaction equation

HRID 2192322 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([CH2:16][CH2:17][CH:18]=[CH2:19])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[CH2:5][CH2:6]C=C>ClCCl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:1][O:2][C:3]([C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:5][CH2:6][CH:19]=[CH:18][CH2:17][CH2:16]1)=[O:20]

Participants

4

Reactant 1

HCID 58348421HCID 58348421, compound

Product 1

HCID 58348350HCID 58348350, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2-but-3-enyl-2-(3-fluoro-phenyl)-hex-5-enoic acid methyl ester (Example 12a) (5.0 g) in dichloromethane (100 mL) was added Grubbs Catalyst (2nd Generation, Sigma-Aldrich Company Ltd) (0.05 g). The mixture was warmed to reflux under nitrogen. After 20 hours the reaction was cooled to room temperature, evaporated to an oil and purified by column chromatography on silica eluting with ethyl acetate/isohexane (5/95) to yield an oil. Analysis of the product showed that significant amounts of starting material was present in the mixture so the mixture was subjected to a repetition of the reaction conditions and purification as above to afford the subtitled compound as a coloured oil (3.60 g).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux under nitrogen
  3. customevaporated to an oil
  4. custompurified by column chromatography on silica eluting with ethyl acetate/isohexane (5/95)
  5. customto yield an oil
  6. customwas subjected to a repetition of the reaction conditions and purification as above

Sources & evidence

ORD record
ord-d0b5ed7d6bd94bb28f8d69df9db62304
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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