Hydrochloric Acid → 2-(4-(2-fluoroethoxy)-3-hydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one

HRID 1879560Notes

Reaction equation

HRID 1879560 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:18]([C:19](=[O:25])[C:20]=2[O:21]COC)=[CH:17][CH:16]=[C:15]([O:26]COC)[CH:14]=3)=[CH:7][C:6]=1[O:30]COC.Cl>O1CCOCC1>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:18]([C:19](=[O:25])[C:20]=2[OH:21])=[CH:17][CH:16]=[C:15]([OH:26])[CH:14]=3)=[CH:7][C:6]=1[OH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866513762-(4-(2-fluoroethoxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one

Product 1

HCID 581602292-(4-(2-fluoroethoxy)-3-hydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-(4-(2-fluoroethoxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one (19 mg, 0.041 mmol) was added 1 mL of 4 M HCl solution in dioxane. The mixture was stirred at rt for 3 h. Volatiles were removed under reduced pressure and the residue was washed with ether (2×1 mL) and dried under high vacuum to afford 2-(4-(2-fluoroethoxy)-3-hydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one (AD-F-001S-WZ01067) as a yellow solid (11 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 9.39 (s, 1H), 9.17 (s, 1H), 7.89 (d, J=9.6 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.59 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 6.87 (m, 2H), 4.80 (m, 1H), 4.68 (m, 1H), 4.30 (m, 1H), 4.23 (m, 1H); MS (ESI) m/z 333 (M+H+), 355 (M+Na+).

Workup

  1. customVolatiles were removed under reduced pressure
  2. washthe residue was washed with ether (2×1 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-4b48baff2f2b47d2842611cd0e7084dd
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

Loading…