Dichloromethane → 2-(5,6,7,8-Tetrahydro-1-naphthoxy)-1-tetrahydropyranyloxyethane

HRID 2371638Notes

Reaction equation

HRID 2371638 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.C(Cl)Cl.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]1([O:11][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 151574992-(5,6,7,8-Tetrahydro-1-naphthoxy)-1-tetrahydropyranyloxyethane

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 1.48 g (10 mmol) of 5,6,7,8-tetrahydro-1-naphthol, 0.34 g (1.0 mmol) of tetra-n-butylammonium hydrogen sulfate, 6.27 (30 mmol) of the title product of Example 57, 20 ml of methylene chloride, 9 ml of water, and 11 ml of 1N sodium hydroxide was stirred vigorously overnight at reflux. The organic layer was separated, and the solvent removed under reduced pressure. The residue was triturated with diethyl ether and filtered to remove the insolubles. The ether solution was sequentially washed with two portions of dilute aqueous sodium hydroxide, with water, and then with brine. After drying over magnesium sulfate, the solution was filtered and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel, using 5% ethyl acetate/hexane as eluent gave 730 mg of the title compound.

Workup

  1. temperatureat reflux
  2. customThe organic layer was separated
  3. customthe solvent removed under reduced pressure
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered
  6. customto remove the insolubles
  7. washThe ether solution was sequentially washed with two portions of dilute aqueous sodium hydroxide, with water
  8. dry with materialAfter drying over magnesium sulfate
  9. filtrationthe solution was filtered
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cc9e41fabe3d489db1752cfe630ced65
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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