p-Toluenesulfonic acid → HCID 13150727, compound

HRID 2166852Notes

Reaction equation

HRID 2166852 reaction equation
[C:1]12[CH2:7][CH:5]([CH2:6]1)[CH2:4][CH2:3][CH:2]=2.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(O)(=O)=[O:21])=CC=1.C(Cl)Cl.C(N([CH2:33][CH3:34])CC)C>>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[O:21][CH2:33][CH2:34][C:2]1[CH:1]2[CH2:7][CH:5]([CH2:4][CH:3]=1)[CH2:6]2

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 22022240HCID 22022240, compound

Product 1

HCID 13150727HCID 13150727, compound

Procedure

A mixture of 600 mg of the norpinene compound (prepared in Reference Example 2), 0.5 ml of 2,3-dihydropyran, a catalytic amount of p-toluenesulfonic acid and 10 ml of methylene chloride was stirred at room temperature for 30 minutes. 0.2 ml of triethylamine was added to the reaction mixture, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography using a mixture of cyclohexane and ethyl acetate (49:1) as an eluent to obtain 812 mg of the titled compound.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customThe residue was purified by silica gel column chromatography
  3. additiona mixture of cyclohexane and ethyl acetate (49:1) as an eluent

Sources & evidence

ORD record
ord-1cf4540a72ca4109b7189c2645d7647a
Source dataset
uspto-grants-1983_06
Patent number
US04389413

Reaction notes

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