Hydrochloric Acid → HCID 18694197, compound

HRID 1870994Notes

Reaction equation

HRID 1870994 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[O:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7][C:6]=2[CH:13]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.Cl>CC(O)C.ClC(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[CH2:8][CH2:7][C:6]=2[CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 18694150HCID 18694150, compound

Product 1

HCID 18694197HCID 18694197, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of intermediate 14-b (0.25 mol), 3,4-dihydro-2H-pyran (0.50 mol) and hydrochloric acid in 2-propanol (0.5 ml) in trichloromethane (700 ml) was stirred for 3 h on a water bath. The reaction mixture was washed with a 10% NaOH solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 81 g of (±)-6-fluoro-3,4-dihydro-8-nitro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran (104% crude residue) (interm. 15-b).

Workup

  1. washThe reaction mixture was washed with a 10% NaOH solution
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d9f161ea1d9c4a18a2708e4083140489
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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