Cesium carbonate → 2,5,7-Trimethyl-1-oxo-6-vinyl-indan-2-carboxylic acid ethyl ester

HRID 473069Notes

Reaction equation

[CH:1]([B-](F)(F)F)=[CH2:2].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:33]([O:35][C:36]([C:38]1([CH3:51])[CH2:46][C:45]2[C:40](=[C:41]([CH3:49])[C:42](Br)=[C:43]([CH3:47])[CH:44]=2)[C:39]1=[O:50])=[O:37])[CH3:34]>C1COCC1.O.O.Cl[Pd]Cl>[CH2:33]([O:35][C:36]([C:38]1([CH3:51])[CH2:46][C:45]2[C:40](=[C:41]([CH3:49])[C:42]([CH:1]=[CH2:2])=[C:43]([CH3:47])[CH:44]=2)[C:39]1=[O:50])=[O:37])[CH3:34]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of potassium vinyltrifluoroborate (0.186 g, 1.38 mmol), PdCl2, (0.033 g, 0.18 mmol), PPh3 (0.073 g, 0.27 mmol), Cs2CO3 (1.2 g, 3.69 mmol) and compound 5 (0.3 g, 0.92 mmol) in THF/H2O (9:1) (3 mL) was heated at 85° C. under an Argon atmosphere in a sealed tube. The reaction mixture was stirred at 85° C. for 48 h, then cooled to room temperature and diluted with H2O (6 mL) followed by extraction with ethyl acetate (30 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 2 to 4% EtOAc in petroleum ether eluant) gave pure compound 6 (0.23 g, 92%).

Workup

temperaturecooled to room temperature
extractionfollowed by extraction with ethyl acetate (30 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customPurification by column chromatography (SiO2, 2 to 4% EtOAc in petroleum ether eluant)

Sources & evidence

ORD record: ord-8a432d8f92434016ac1f0bee56d05d5e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633252B2

Reaction notes

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