Potassium Carbonate → HCID 59189511, compound

HRID 1686860Notes

Reaction equation

HRID 1686860 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][C@H:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])[CH:14]([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+]>CO>[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C@@H:13]([OH:12])[CH:14]([CH3:15])[CH3:16])([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86639077HCID 86639077, compound

Product 1

HCID 59189511HCID 59189511, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-(2-Nitrophenyl)-2-methyl-propyl (1S)-camphanate (0.717 g, 1.90 mmol) was dissolved in hot methanol (40 mL) and K2CO3 (0.380 g, 2.74 mmol) was added. The mixture was heated to reflux for one hour, then cooled down, concentrated in vacuo, and diluted with diethyl ether (100 mL). The organic phase was washed with water (20 mL), dried over anhydrous Na2SO4, and purified by silica gel column chromatography to yield (S)-1-(2-nitrophenyl)-2-methyl-propanol (0.360 g, 97%) 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. temperaturecooled down
  4. concentrationconcentrated in vacuo
  5. additiondiluted with diethyl ether (100 mL)
  6. washThe organic phase was washed with water (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7268f28f627e41609b8a33db492203a2
Source dataset
uspto-grants-2012_04
Patent number
US08148503B2

Reaction notes

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