1,4-Dioxane hydrochloride → HCID 58160197, compound

HRID 1879551Notes

Reaction equation

HRID 1879551 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([O:22]C2CCCCO2)=[CH:7][CH:8]=[C:9]2[C:14]=1[O:13][C:12](=[O:15])[CH:11]=[C:10]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O1CCOCC1.Cl>>[F:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([OH:22])=[CH:7][CH:8]=[C:9]2[C:14]=1[O:13][C:12](=[O:15])[CH:11]=[C:10]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86651375HCID 86651375, compound

Product 1

HCID 58160197HCID 58160197, compound

Procedure

To 8-(2-fluoroethoxy)-4-phenyl-7-(tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one was added 1.5 mL of a 4 M HCl dioxane solution. The mixture was stirred at rt for 30 min under Ar atmosphere and concentrated. The crude product was purified with chromatography (hexane/EtOAc) to afford 8-(2-fluoroethoxy)-7-hydroxy-4-phenyl-2H-chromen-2-one (AD-C-004S-WZ01055) as a white solid (24 mg, 90%). 1H NMR (400 MHz, CDCl3) δ 8.96 (s, 1H), 7.57-7.54 (m, 3H), 7.52-7.49 (m, 2H), 7.08 (dd, J=8.8, 1.2 Hz, 1H), 6.87 (dd, J=8.8, 1.2 Hz, 1 H), 6.11 (d, J=1.2 Hz, 1H), 4.86 (m, 1H), 4.74 (m, 1H), 4.50 (m, 1H), 4.43 (m, 1H); MS (ESI) m/z 301 (M+H+), 323 (M+H+).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified with chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-8a3178519bb94ad0a5d19a2176b78f04
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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