Trifluoroacetic acid → 5-ethyl-5-hydroxy-9-methoxy-4,5-dihydrooxepino[3,4-c]pyridin-3(1H)-one

HRID 1007864Notes

Reaction equation

HRID 1007864 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH3:20])[C:14]=1[CH2:21][OH:22])([CH2:11][CH3:12])[CH2:3][C:4]([O:6]C(C)(C)C)=O.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:11]([C:2]1([OH:1])[C:13]2[C:14](=[C:15]([O:19][CH3:20])[N:16]=[CH:17][CH:18]=2)[CH2:21][O:22][C:4](=[O:6])[CH2:3]1)[CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21891952Tert-butyl 3-hydroxy-3-[3-(hydroxymethyl)-2-methoxy-4-pyridinyl]pentanoate

Product 1

HCID 105618445-ethyl-5-hydroxy-9-methoxy-4,5-dihydrooxepino[3,4-c]pyridin-3(1H)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-butyl 3-hydroxy-3-[3-(hydroxymethyl)-2-methoxy-4-pyridinyl]pentanoate (8.8 g, 28 mmol) is treated with trifluoroacetic acid (30 ml) for 3 hours at ambient temperature. The volatile components are evaporated off and the residue is purified by column chromatography (SiO2, CH2Cl2/MeOH: 100/0 to 98/2), which produces a limpid oil which, after treatment with toluene, produces 5.9 g of product (L) (89%) in the form of white crystals, m.p. 97-98° C.

Workup

  1. customThe volatile components are evaporated off
  2. customthe residue is purified by column chromatography (SiO2, CH2Cl2/MeOH: 100/0 to 98/2), which
  3. customproduces a limpid oil which

Sources & evidence

ORD record
ord-1f296a28371c4c47ae64d0157e011508
Source dataset
uspto-grants-2004_09
Patent number
US06797715B1

Reaction notes

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