Pyridine → HCID 10802961, compound

HRID 1257076Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CC=CC=1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20].CCOC(C)=O>C(Cl)Cl>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=1[O:1][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18])=[O:5]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 2-hydroxy-4-methoxy-benzaldehyde (30 g, 197 mmol) in DCM (anhydrous, 120 mL) was added pyridine (79 mL, 986 mmol) at room temperature. After the mixture was cooled to −10° C., the Tf2O (50 mL, 296 mmol) was slowly added to the reaction between −10° C. to 0° C. The addition took about 2.5 hours. After the addition, the stirring was kept for 30 minutes. The EtOAc (200 mL) was added. The organic layer was washed with 1 M HCl (3×80 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified over silica gel, eluting with 5% EtOAc/hexanes to give trifluoro-methanesulfonic acid 2-formyl-5-methoxy-phenyl ester (2) 46 g in 82% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.13 (s, 1 H), 7.95 (d, J=8.99 Hz, 1 H), 7.03 (dd, J=8.60, 2.34 Hz, 1 H), 6.88 (d, J=2.34 Hz, 1 H), 3.93 (s, 3 H)

Workup

additionThe addition
additionAfter the addition
waitthe stirring was kept for 30 minutes
washThe organic layer was washed with 1 M HCl (3×80 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum
customThe residue was purified over silica gel
washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record: ord-e2edd03b4ec545e0824546a3f41a53b1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461336B2

Reaction notes

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