p-Toluenesulfonic acid → HCID 54464049, compound

HRID 569641Notes

Reaction equation

HRID 569641 reaction equation
O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23](=[O:37])[CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)[CH:11]=[CH:12][C:13]=1[O:14]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(N(CC)CC)C>[OH:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23](=[O:37])[CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)[CH:11]=[CH:12][C:13]=1[OH:14]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54299131HCID 54299131, compound

Product 1

HCID 54464049HCID 54464049, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 887MethanolSolvent

Procedure

In 5 ml of absolute methanol was dissolved 100 mg of 1-(3,4-bistetrahydropyranyloxyphenyl)-6-(3,4-dimethoxyphenyl)-3-oxo-1-hexene obtained in Example 15-(1). A catalytic amount of p-toluenesulfonic acid was added to the solution at 0° C. and a stirring was effected at the same temperature for 1 hour. After the reaction, 1 drop of triethylamine was added to the reaction mixture and then the mixture was concentrated to give crude product. By purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=1:1), 55 mg of the above caption compound was obtained.

Workup

  1. additionwas added to the reaction mixture
  2. concentrationthe mixture was concentrated
  3. customto give crude product
  4. customBy purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f85d6680a8924c929a61cbb19c1bdbff
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

Loading…