3,4-dihydro-2H-pyran → Methyl 6-[(2-tetrahydropyranyl)oxymethyl]-5,6,7,8-tetrahydro-2-naphthalenecarboxylate

HRID 1901317Notes

Reaction equation

HRID 1901317 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:6][C:5]=2[CH2:4]1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1>S(=O)(=O)(O)O.C(OCC)C>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:6][C:5]=2[CH2:4]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyran2×HCID 13851838Methyl 6-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate

Product 1

HCID 21844324Methyl 6-[(2-tetrahydropyranyl)oxymethyl]-5,6,7,8-tetrahydro-2-naphthalenecarboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

10.0 g of methyl 6-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was added to 3.82 g of 2,3-dihydropyrane. After further adding 5 drops of concentrated sulfuric acid, the resulting mixture was stirred for 1 hour. To this were further added 1.00 g of 2,3-dihydropyrane and 3 drops of concentrated sulfuric acid, followed by stirring for 5 hours. The resulting reaction mixture was mixed with 100 ml of diethyl ether, and the mixture was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order, followed by drying. By distilling off the solvent, 13.72 g of methyl 6-[(2-tetrahydropyranyl)oxymethyl]-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was obtained in the form of yellow oil.

Workup

  1. stirringby stirring for 5 hours
  2. customThe resulting reaction mixture
  3. washthe mixture was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order
  4. customby drying
  5. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-9886009ca187403bb79a0f5ed9b20010
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

Loading…