Triethylamine → HCID 87093775, compound

HRID 420822Notes

Reaction equation

HRID 420822 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:2].CCN(CC)CC.[O:22](S(C(F)(F)F)(=O)=O)[S:23]([C:26]([F:29])([F:28])[F:27])(=O)=[O:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:24])=[O:22])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 21322395Ethyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 87093775HCID 87093775, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve the ethyl 3-cyano-4-hydroxy-benzoate (22.36 g, 117.1 mmoles) in anhydrous CH2Cl2 (400 mL) at 0° C. Add Et3N (24.3 mL, 175.6 mmoles), DMAP (2.14 g, 17.5 mmol), and dropwise Tf2O (49.5 g, 175.6 mmoles). Stir the mixture at room temperature for 2 hours. Concentrate the mixture under reduced pressure and subject residue to silica gel chromatography eluting hexane/EtOAc 4:1, to obtain 34.99 g of ethyl 3-cyano-4-trifluoromethanesulfonyloxy-benzoate (92% yield). MS(ES): m/z=190.0 [M-H].

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. washeluting hexane/EtOAc 4:1

Sources & evidence

ORD record
ord-d25c8fafad4a41a7852d3577da9abd3b
Source dataset
uspto-grants-2012_01
Patent number
US08097652B2

Reaction notes

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