Hexane → HCID 10220533, compound

HRID 431901Notes

Reaction equation

HRID 431901 reaction equation
FC(F)(F)S([C:6]1[CH:7]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=O)=O.[C-:25]#[N:26].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC>C(#N)C.[Zn].C(OCC)(=O)C>[C:25]([C:6]1[CH:7]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=2)[CH:9]=[CH:10][CH:11]=1)#[N:26]

Participants

8

Reactant 4

HCID 8058HexaneHCID 9032Potassium CyanideHCID 11776TriphenylphosphineHCID 21942418HCID 21942418, compound

Product 1

HCID 10220533HCID 10220533, compoundYield 23.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-[3-trifluoromethanesulfonylphenyl]-3-[pyridin-2-yl]-1,2-oxazole (98 mg, 0.26 mmol), KCN (230 mg, 4 mmol), NiBr2(PPh3)2 (52.4 mg, 0.07 mmol), and PPh3 (42 mg, 0.16 mmol) in acetonitrile (1 mL) was treated with zinc powder (20 mg, 0.3 mmol) and the mixture was heated overnight at 60° C. Silica gel chromatography of the resulting mixture using a gradient of hexane to ethyl acetate afforded 15 mg (23%) of 5-[3-cyanophenyl]-3-[pyridin-2-yl]-1,2-oxazole as a white solid.

Sources & evidence

ORD record
ord-8ed7f1511cdc428ea9ea49f5ec7ef3cb
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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