Ethyl Acetate → HCID 22493004, compound

HRID 1816350Notes

Reaction equation

HRID 1816350 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])(=O)=O)=CC=1.C(OCC)(=O)C>CN(C)C=O.O>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 22492958HCID 22492958, compound

Product 1

HCID 22493004HCID 22493004, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (9.5 g) in N,N-dimethylformamide (200 ml) was added portionwise sodium hydride (abt. 60% oil suspension) (2.6 g) under ice-cooling and nitrogen atmosphere. After stirring for 2 hours at room temperature, the reaction mixture was stirred for 1 hour at 60° C. To the reaction mixture was added a solution of 7-methoxyheptyl 4-methylbenzenesulfonate (15.0 g) in N,N-dimethylformamide (50 ml) at 60° C. and then the reaction mixture was stirred for 2 hours at 60° C. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1→5:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 8-(7-methoxyheptyloxy)-1,4-dioxaspiro[4.5]decane (9.77 g).

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred for 1 hour at 60° C
  3. stirringthe reaction mixture was stirred for 2 hours at 60° C
  4. temperatureAfter being cooled to room temperature
  5. washThe organic layer was successively washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1→5:1)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-74ccd413ceed465a9cd8c7671d15222a
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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