p-Toluenesulfonic acid → (1R,5R)-10-(tetrahydropyran-2-yloxy)methyl-2-pinene

HRID 414573Notes

Reaction equation

HRID 414573 reaction equation
[C:1]12[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]=2[CH3:10].[O:11]1[CH:16]=C[CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.C(N([CH2:33][CH3:34])CC)C>C(Cl)Cl>[O:24]1[CH2:34][CH2:33][CH2:14][CH2:13][CH:12]1[O:11][CH2:16][CH2:10][C:2]1[C@@H:1]2[CH2:9][C@@H:5]([CH2:4][CH:3]=1)[C:6]2([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 15837102(-)-Pinene

Product 1

HCID 22840917(1R,5R)-10-(tetrahydropyran-2-yloxy)methyl-2-pinene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pinene (15.5 g) prepared in reference example 1 in methylene chloride (300 ml), 2,3-dihydropyran (9.4 ml) was dropped. After addition of catalytic amount of p-toluenesulphonic acid, the solution was stirred at room temperature. After reaction, triethylamine was added to the solution. The solution was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (cyclohexane: ethyl acetate=99:1) to give the title compound (20.8 g) having the following physical data:

Workup

  1. additionwas added to the solution
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (cyclohexane: ethyl acetate=99:1)

Sources & evidence

ORD record
ord-2546ea5de1c749aca9f70644fc75ea36
Source dataset
uspto-grants-1988_12
Patent number
US04792550

Reaction notes

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