2-But-3-enyl-2-thiophen-2-yl-hex-5-enoic acid ethyl ester → 1-Thiophen-2-yl-cyclohept-4-enecarboxylic acid ethyl ester

HRID 2192307Notes

Reaction equation

HRID 2192307 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH2:15][CH2:16][CH:17]=[CH2:18])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:6][CH2:7]C=C)[CH3:2]>ClCCl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH2:1]([O:3][C:4]([C:5]1([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:7][CH:18]=[CH:17][CH2:16][CH2:15]1)=[O:19])[CH3:2]

Participants

4

Reactant 1

HCID 583483872-But-3-enyl-2-thiophen-2-yl-hex-5-enoic acid ethyl ester

Product 1

HCID 583483311-Thiophen-2-yl-cyclohept-4-enecarboxylic acid ethyl esterYield 90.9%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2-but-3-enyl-2-thiophen-2-yl-hex-5-enoic acid ethyl ester (Example 5a) (3.18 g) in dichloromethane (100 mL) was added Grubbs Catalyst (2nd Generation, Sigma-Aldrich Company Ltd) (0.100 g). The mixture was warmed to reflux under nitrogen. After 20 hours the mixture was allowed to cool to room temperature and evaporated to an oil. Purification by column chromatography on silica eluting with ethyl acetate/isohexane (10:90) to yield the sub-titled compound (2.60 g) as a coloured oil.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux under nitrogen
  3. customevaporated to an oil
  4. customPurification by column chromatography on silica eluting with ethyl acetate/isohexane (10:90)

Sources & evidence

ORD record
ord-db7140eed88d4096bb5b9e4006b573e6
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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