Ammonia → 1-(2-Hydroxyethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

HRID 1250275Notes

Reaction equation

HRID 1250275 reaction equation
N.C([O:9][CH2:10][CH2:11][C:12]12[O:19][CH2:18][C:15]([CH3:20])([CH2:16][O:17]1)[CH2:14][O:13]2)C1C=CC=CC=1.[Na].[Cl-].[NH4+]>O1CCCC1>[OH:9][CH2:10][CH2:11][C:12]12[O:13][CH2:14][C:15]([CH3:20])([CH2:16][O:17]1)[CH2:18][O:19]2

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 183273631-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane

Product 1

HCID 183273721-(2-Hydroxyethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octaneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To liquid ammonia (35 ml) was added, under an argon atmosphere, a solution of 1-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane (3.54 g) in anhydrous tetrahydrofuran (8 ml). Metallic sodium (500 mg) was then added thereto, and the resultant mixture was stirred for 3 hours at −78° C. After ammonium chloride was added to the reaction mixture, ammonia was evaporated, and tetrahydrofuran was evaporated under reduced pressure. The residue was washed with ether, and the resultant solid was added to saturated brine and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give 1-(2-hydroxyethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (1.4 g) as a pale yellow oil.

Workup

  1. customwas evaporated
  2. customtetrahydrofuran was evaporated under reduced pressure
  3. washThe residue was washed with ether
  4. additionthe resultant solid was added to saturated brine
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e1a91ee541bb4ea2a1961a39219e41d1
Source dataset
uspto-grants-2002_01
Patent number
US06337334B1

Reaction notes

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