Tetrahydro-2-(2-propynyloxy)-2H-pyran → 6-Methoxy-2-p-methoxyphenyl-1,2,3,4-tetrahydro-1-(3-tetrahydropyranyloxypropynyl)naphth-1-ol

HRID 1200083Notes

Reaction equation

HRID 1200083 reaction equation
C[Mg]I.[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:10][CH2:11][C:12]#[CH:13].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[CH:21]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[CH2:20][CH2:19]2>O1CCCC1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:13]#[C:12][CH2:11][O:10][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][O:4]1)([OH:26])[CH:21]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 134065432-(4-Methoxyphenyl)-6-methoxy-1-tetraloneHCID 178418373HCID 178418373, compound

Product 1

HCID 198644436-Methoxy-2-p-methoxyphenyl-1,2,3,4-tetrahydro-1-(3-tetrahydropyranyloxypropynyl)naphth-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of methyl magnesium iodide (22.3 ml. of a 2.86 molar solution in tetrahydrofuran) was added dropwise to a stirred solution of the propargyl tetrahydropyranyl ether thus obtained (10.0 g.) in tetrahydrofuran (200 ml.) which was maintained under an atmosphere of argon, and the mixture was heated under reflux for 30 minutes. A solution of 3,4-dihydro-6-methoxy-2-p-methoxyphenylnaphthalen-1(2H)-one (7.2 g.; prepared by the method described in the Journal of Medicinal Chemistry, 1966, 9, 172) in tetrahydrofuran (100 ml.) was added to the boiling solution and the mixture was heated under reflux for 30 minutes, cooled and poured into ice-cold saturated aqueous ammonium chloride solution (300 ml.). The mixture was extracted three times with diethyl ether (150 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 5:1 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 6-methoxy-2-p-methoxyphenyl-1,2,3,4-tetrahydro-1-(3-tetrahydropyranyloxypropynyl)naphth-1-ol.

Workup

  1. temperaturewas maintained under an atmosphere of argon
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. customprepared by the method
  5. additionwas added to the boiling solution
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 30 minutes
  8. temperaturecooled
  9. extractionThe mixture was extracted three times with diethyl ether (150 ml
  10. washeach time) and the combined extracts were washed with water
  11. customdried
  12. customevaporated to dryness
  13. customThe residue was purified by chromatography on a silica gel column
  14. additiona 5:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-24fa58e8f11b4d44af77a4647e83cb09
Source dataset
uspto-grants-1990_02
Patent number
US04904661

Reaction notes

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