Potassium Carbonate → HCID 86684717, compound

HRID 339223Notes

Reaction equation

HRID 339223 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][C@H:13]([C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([I:26])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28])[C:14]([CH3:17])([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+]>CO>[I:26][C:21]1[C:22]([O:24][CH3:25])=[CH:23][C:18]([C@@H:13]([OH:12])[C:14]([CH3:17])([CH3:16])[CH3:15])=[C:19]([N+:27]([O-:29])=[O:28])[CH:20]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86684718HCID 86684718, compound

Product 1

HCID 86684717HCID 86684717, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-1-(4-iodo-5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (1.1 g, 2.0 mmol) and K2CO3 (552 mg, 4.0 mmol) in methanol (50 mL) was heated to reflux for one hour, then cooled down, concentrated in vacuo, and diluted with CH2Cl2 (50 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield enantiopure (S)-1-(4-iodo-5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propanol (720 mg, 98%). 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 1H, Ph-H), 7.17 (s, 1H, Ph-H), 5.60 (d, 1H, J=4.0 Hz, PhCH), 3.98 (s, 3H, OCH3), 2.12 (d, 1H, J=4.0 Hz, OH), 0.89 (s, 9H,C(CH3)3).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour
  3. temperaturecooled down
  4. concentrationconcentrated in vacuo
  5. additiondiluted with CH2Cl2 (50 mL)
  6. washThe organic phase was washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18d65a20a4354eb7a3fdc9eabc6d276c
Source dataset
uspto-grants-2014_11
Patent number
US08889860B2

Reaction notes

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