Hydrochloric Acid → 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl) benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran hydrochloride

HRID 1291054Notes

Reaction equation

HRID 1291054 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])=[CH:20][CH:19]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.[ClH:30].CO>C(Cl)Cl>[ClH:30].[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])=[CH:20][CH:19]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 103860554-(5-fluoro-3-(4-(2-methyl-1H-imidazol-1-yl)benzyloxy)phenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran

Product 1

HCID 189201954-[5-fluoro-3-[4-(2-methylimidazol-1-yl) benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl) benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran (0.5 g, 1.3 mmol) in dry CH2Cl2 (5 ml) was added "Hydrogen Chloride; Methanol Reagent 10" (4 ml, Tokyo Chemical Industries) at ambient temperature. After stirring for 10 minutes solvent was removed under reduced pressure. The crude product was recrystallized from isopropyl alcohol (4 ml) -ethanol (3 ml) to give 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl) benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran hydrochloride (0.3 g, 55%) as white solids.

Workup

  1. customat ambient temperature
  2. customwas removed under reduced pressure
  3. customThe crude product was recrystallized from isopropyl alcohol (4 ml) -ethanol (3 ml)

Sources & evidence

ORD record
ord-eed80e6c5ae8460995851dccfa25f293
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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