Potassium Carbonate → HCID 86598699, compound

HRID 2377207Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][C:12]([CH3:20])([CH3:19])[C:11]=2[CH:10]=[C:9]([CH:21]=[O:22])[CH:8]=1)(=O)=O.B(O)(O)[C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=1.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH3:18][C:15]1([CH3:17])[CH2:14][CH2:13][C:12]([CH3:19])([CH3:20])[C:11]2[CH:10]=[C:9]([CH:21]=[O:22])[CH:8]=[C:7]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:16]1=2

Participants

Conditions

Temperature: 90 °C

Procedure

1.4 g (3.8 mmol) of 3-formyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1-naphthyl 1,1,1-trifluoromethanesulfonate are dissolved in 50 mL of DME, followed by 625 mg (4.6 mmol) of p-tolylboronic acid. 485 mg (11.4 mmol) of lithium chloride and 4.6 mL (9.2 mmol) of 2 M potassium carbonate solution are added to the reaction medium, which is then degassed with a flow of nitrogen and then heated to 90° C. 220 mg of tetrakis(triphenylphosphine)palladium are added and the reaction medium is stirred at reflux for 20 hours, then hydrolysed and extracted with ethyl acetate. The residue obtained is purified by chromatography, to give an orange-colored oil (m=980 mg; yield=85%).

Workup

customis then degassed with a flow of nitrogen
addition220 mg of tetrakis(triphenylphosphine)palladium are added
temperatureat reflux for 20 hours
extractionhydrolysed and extracted with ethyl acetate
customThe residue obtained
customis purified by chromatography
customto give an orange-colored oil (m=980 mg; yield=85%)

Sources & evidence

ORD record: ord-1eb7e303ecfb48e8a8920ede4a9a58f0
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468457B2

Reaction notes

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