Sodium Iodide → HCID 11538196, compound

HRID 1018300Notes

Reaction equation

HRID 1018300 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6](=[O:18])[CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)[CH3:2].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:29][C:30](=[O:31])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:6](=[O:18])[CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 53802767HCID 53802767, compound

Product 1

HCID 11538196HCID 11538196, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 4-adamantan-1-yl-3-oxo-butyric acid ethyl ester, prepared by a modification of Wierenga and Skulnick's procedure (W. Wierenga and H. I. Skulnick, J. Org. Chem., 1979, 44, 310)(3.00 g, 11.0 mmol) in acetone (30 ml) was added sodium iodide (0.55 g, 3.67 mmol) and anhydrous potassium carbonate (3.04 g, 22.0 mmol), then a solution of 2-bromo-1-phenyl-ethanone (2.38 g, 11.5 mmol) in acetone (10 ml). The mixture was stirred at reflux for 36 h, cooled to room temperature and filtered. The filtrate was evaporated, the residue was dissolved in diethyl ether (50 ml) and washed with water (2×20 ml). The organic phase was dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, hexane/ethyl acetate 4:1) to afford the product as pale yellow oil (1.92 g, 46%). 1H NMR (300 MHz, CDCl3) 7.98 (2H, m), 7.65 (1H, m), 7.46 (2H, m), 4.19 (3H, m), 3.60 (1H, dd), 5.59 (1H, dd), 2.50 (2H, dd), 1.96 (3H, br s), 1.68 (12H, m), 1.29 (3H, t).

Workup

  1. temperatureat reflux for 36 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in diethyl ether (50 ml)
  5. washwashed with water (2×20 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was evaporated
  8. customThe residue was purified by flash column chromatography (silica, hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-46b6cf9c035f4b35b867ea0c09a6c8cd
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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