Potassium Carbonate → HCID 59189553, compound

HRID 1686865Notes

Reaction equation

HRID 1686865 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-d045a08ae98f4c3a8cda3b76454d23bb
Source dataset
uspto-grants-2012_04
Patent number
US08148503B2

Reaction notes

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