Triethylamine → 2-Methyl-2-[(2-chloroethoxy)methoxy]adamantane

HRID 749647Notes

Reaction equation

HRID 749647 reaction equation
Cl[CH2:2][O:3][CH2:4][CH2:5][Cl:6].[CH3:7][C:8]1([OH:18])[CH:15]2[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:17][CH:9]1[CH2:10]3)[CH2:14]2.C(N(CC)CC)C>C1COCC1>[CH3:7][C:8]1([O:18][CH2:2][O:3][CH2:4][CH2:5][Cl:6])[CH:9]2[CH2:17][CH:13]3[CH2:12][CH:11]([CH2:16][CH:15]1[CH2:14]3)[CH2:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1365452-Methyl-2-adamantanolHCID 102908101-Chloro-2-(chloromethoxy)ethane

Product 1

HCID 691991932-Methyl-2-[(2-chloroethoxy)methoxy]adamantaneYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A two neck Kjeldahl flask of 50 ml into which a stirrer was put was charged with 1.55 g (12 mmol) of chloroethyl chloromethyl ether obtained in Example 1 (1), 1.66 g (10 mmol) of 2-methyl-2-adamantanol, 1.52 g (15 mmol) of triethylamine and dried THF, and it was equipped with a coiled condenser to reflux and stir the solution for 8 hours. Triethylamine hydrochloride was filtered, and gas chromatographic analysis was carried out to find that 2-methyl-2-adamantanol was converted by 46.2% and that 2.04 g (7.9 mmol, isolation yield: 78.8%) of a colorless liquid which was the intended product was obtained at a selectivity of 97.3%.

Workup

  1. customwas equipped with a coiled condenser
  2. temperatureto reflux
  3. filtrationTriethylamine hydrochloride was filtered
  4. customwas obtained at a selectivity of 97.3%

Sources & evidence

ORD record
ord-abb86111c30d46a7a026086e0c0dd218
Source dataset
uspto-grants-2008_07
Patent number
US07402712B2

Reaction notes

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