Sodium Carbonate → 2-(Tricyclo[3.3.1.1~3,7~]decan-1-yl)oxirane

HRID 2302108Notes

Reaction equation

HRID 2302108 reaction equation
[CH:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2)=[CH2:2].C(=O)([O-])[O-:14].[Na+].[Na+]>ClCCl>[O:14]1[CH2:2][CH:1]1[C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 5709341-Vinyladamantane

Product 1

HCID 146126312-(Tricyclo[3.3.1.1~3,7~]decan-1-yl)oxiraneYield 123.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 16.2 g of 1-vinyladamantane, 120 ml of dichloromethane, and 5.3 g of sodium carbonate, 36.9 g of 70-m-chloroperbenzoic acid was added over 30 minutes on a water bath. The resultant mixture was stirred at room temperature for further 2 hours, was washed with a 5% sodium sulfite aqueous solution and saturated aqueous sodium bicarbonate, and the obtained organic layer was then concentrated. The residue was purified by column chromatography on a silica gel (SiO2400 g, developing solution: hexane/ethyl acetate=15/1) to give 11.0 g of 1-(1,2-epoxyethyl)adamantane.

Workup

  1. additionwas added over 30 minutes on a water bath
  2. washwas washed with a 5% sodium sulfite aqueous solution and saturated aqueous sodium bicarbonate
  3. concentrationthe obtained organic layer was then concentrated
  4. customThe residue was purified by column chromatography on a silica gel (SiO2400 g, developing solution: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-19bb86e928204a0eae309bb5a3147f14
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Reaction notes

Loading…