1-Bromo-3,5-dimethyladamantane → HCID 22633608, compound

HRID 365632

Reaction equation

HRID 365632 reaction equation
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4](Br)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>C(O)(=O)C>[C:14]([O:17][C:4]12[CH2:3][C:2]3([CH3:1])[CH2:12][CH:6]([CH2:7][C:8]([CH3:11])([CH2:9]3)[CH2:10]1)[CH2:5]2)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 983171-Bromo-3,5-dimethyladamantaneHCID 517044Potassium Acetate

Product 1

HCID 22633608HCID 22633608, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.486 (10.2 mmoles) of 3,5-dimethyl-1-bromoadamantane is refluxed for 16 hours with 2.034 g (20.7 mmoles) of potassium acetate in 10 mL of acetic acid. The solution is poured over 100 grams of ice, allowed to melt, and extracted with 3×10 mL of diethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, then dried over sodium sulfate. The solvent is removed under vacuum, yielding 1.521 (67%) of the desired product, a colorless oil. TLC: Rf=0.68 (silica plate: eluant hexane 90%, ethyl acetate 10%). 1HNMR (CDCl3, 500 Mhz): 0.858 (s, 6H), 1.115 (d, 2H, J=12.4 Hz), 1.177 (d, 2H, J=12.4 Hz), 1.260 (d, 2H, J=12.3 Hz), 1.367 (d, 2H, J=12.3 Hz), 1.714 (d, 2H, J=11.6 Hz), 1.766 (d, 2H, J=11.6 Hz), 1.939 (s, 2H), 1.976 (s, 3H), 2.191 (m, 1H).

Workup

  1. extractionextracted with 3×10 mL of diethyl ether
  2. washThe combined ether extracts are washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-199c474a196e4bd9839f8c11963e69b3
Source dataset
uspto-grants-2000_10
Patent number
US06127415

Linked notes

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