Potassium Carbonate → 2-prop-2-enyl-4H-thieno[2,3-c]furan-6-one

HRID 2173202Notes

Reaction equation

Br[C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(CC=C)O1.C(=O)([O-])[O-].[K+].[K+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].CN(C=O)C>[CH2:16]([C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1)[CH:12]=[CH2:11]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 15 mL microwave reaction vial was added 2-bromothieno[2,3-c]furan-6(4H)-one (45 mg, 0.205 mmol), 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane (34.5 mg, 0.205 mmol, 1.0 eq), potassium carbonate (56.8 mg, 0.411 mmol, 2.0 eq) and palladium triphenylphosphane (1:4) (23.7 mg, 0.021 mmol, 0.1 eq). To above mixture was added DMF (1.0 mL), de-gas and filled with N2. The vial was heated to 100° C. for 60 min, cooled down, diluted with EtOAc, washed with aqueous sodium bicarbonate, brine and water. The organic phase was dried over anhydrous Na2SO4, filtered, concentrated. The crude product was purified by flash column chromatography. LC-MS (IE, m/z): 181.2 [M+1]+.

Workup

customIn a 15 mL microwave reaction
customde-gas
additionfilled with N2
temperaturecooled down
additiondiluted with EtOAc
washwashed with aqueous sodium bicarbonate, brine and water
dry with materialThe organic phase was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-1af1281819134703a6b23b055dda2752
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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