HCID 68714946, compound → HCID 57994383, compound

HRID 1875363Notes

Reaction equation

HRID 1875363 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[O:24][CH:23]=[CH:22][C:5]=2[C:6](S(C(F)(F)F)(=O)=O)=[C:7]2[C:12]=1[O:11][C:10]([CH3:13])=[CH:9][C:8]2=[O:14].[Li][CH3:26]>[Zn](Br)Br.O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:24][CH:23]=[CH:22][C:5]=2[C:6]([CH3:26])=[C:7]2[C:12]=1[O:11][C:10]([CH3:13])=[CH:9][C:8]2=[O:14]

Participants

6

Reactant 2

HCID 68714946HCID 68714946, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57994383HCID 57994383, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 91886321HCID 91886321, compoundCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

9-Methoxy-7-methyl-4-trifluoromethanesulfonyl-5H-furo[3,2-g]chromen-5-one (324 mg, 1.0 mmol), ZnBr2.H2O (1.04 g, 4.0 mmol), CuI (28 mg, 0.15 mmol), PdCl2(PPh3)2 (84 mg, 0.12 mmol) and MeLi (2.5 ml of 1.6 M in diethylether, 4.0 mmol) were treated as described under General Procedure G (Step 2) to afford the title compound (Yield 70%). 1H NMR (300 MHz, CDCl3): δ 2.38 (s, 3H, Me), 2.94 (s, 3H, Me), 4.21 (s, 3H, OMe), 6.05 (s, 1H), 6.91 (d, J=2.4, 1H), 7.65 (d, J=2.4, 1H). MS (ES) m/z: 244.9 (M+H+).

Sources & evidence

ORD record
ord-d0cbebc808154bd78e1a199c5abde9d7
Source dataset
uspto-grants-2012_11
Patent number
US08309545B2

Reaction notes

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