Potassium Carbonate → HCID 59189553, compound

HRID 1499647Notes

Reaction equation

HRID 1499647 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][C@H:13]([C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25])[CH:14]([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+]>CO>[I:23][C:20]1[CH:21]=[CH:22][C:17]([C@@H:13]([OH:12])[CH:14]([CH3:15])[CH3:16])=[C:18]([N+:24]([O-:26])=[O:25])[CH:19]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86639079HCID 86639079, compound

Product 1

HCID 59189553HCID 59189553, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propyl (1S)-camphanate (0.288 g, 0.57 mmol) was dissolved in hot methanol (40 mL) and K2CO3 (0.15 g, 1.1 mmol) was added. The mixture was heated to reflux for one hour, cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel column chromatography to yield (S)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propanol (0.184 g, 100%) as a light yellow oil. 1H NMR was identical to that of the racemic alcohol.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-455402684c7c4e649b0786c84a00fd0a
Source dataset
uspto-grants-2015_12
Patent number
US09200319B2

Reaction notes

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