Hydrochloric Acid → HCID 57249218, compound

HRID 982109Notes

Reaction equation

HRID 982109 reaction equation
COC[O:4][C:5]1[C:10]2[CH2:11][C@@H:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:13][C@@H:14]([CH2:15][N+:16]([O-:18])=[O:17])[C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl>CO>[OH:4][C:5]1[C:10]2[CH2:11][C@@H:12]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:13][C@@H:14]([CH2:15][N+:16]([O-:18])=[O:17])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57237145HCID 57237145, compound

Product 1

HCID 57249218HCID 57249218, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 135 mg (0.4 mmol) of [1R,3S] 3,4-dihydro-5-methoxymethoxy-1-nitromethyl-3-phenyl-1H-2-benzopyran, from Step 1, in 5 mL of methanol was saturated with anhydrous hydrogen chloride. The resultant mixture was stirred at reflux temperature for 2 h and then concentrated in vacuo. The residue was purified on silica gel eluted with 5% methanol in methylene chloride to afford 75 mg (66% yield) of the title compound.

Workup

  1. temperatureat reflux temperature for 2 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluted with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-af45e4c68dda4b838e9be04d5a2b2760
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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