Sodium Carbonate → Methyl 5-isopropenyl-4-phenylthiophene-2-carboxylate

HRID 217423Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](B1OC(C)(C)C(C)(C)O1)([CH3:19])=[CH2:18].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH4+].[Cl-]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:17]([C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:19])=[CH2:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 5-bromo-4-phenylthiophene-2-carboxylate in dioxane were added 2-isopropenyl-4,4,5,5-tetramethyl 1,3,2-dioxaborolane and a 2 M aqueous Na2CO3 solution. To the reaction mixture were added palladium acetate and PPh3, followed by stirring at 100° C. for 5 hours. After leaving to be cooled, a saturated aqueous NH4Cl solution was added thereto, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure, followed by purification by silica gel column chromatography (hexane:EtOAc=95:5 to 80:20) to obtain methyl 5-isopropenyl-4-phenylthiophene-2-carboxylate as a colorless liquid.

Workup

customAfter leaving
temperatureto be cooled
extractionfollowed by extraction with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customfollowed by purification by silica gel column chromatography (hexane:EtOAc=95:5 to 80:20)

Sources & evidence

ORD record: ord-91d753e1e34f4132959a8a5fe9a9dfc8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193378B2

Reaction notes

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