p-Toluenesulfonic acid → HCID 54000541, compound

HRID 1612866Notes

Reaction equation

HRID 1612866 reaction equation
[CH2:1]([O:3][C:4]([S:6][C:7]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=1[CH2:9][OH:10])=[S:5])[CH3:2].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([S:6][C:7]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=1[CH2:9][O:10][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:16]1)=[S:5])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 54328324HCID 54328324, compound

Product 1

HCID 54000541HCID 54000541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

38.2 g (0.158 mol) of the compound from Example 7, dissolved in 500 ml of abs. methylene chloride, are treated with 19.8 g (0.24 mol) of dihydropyran and a spatula tipful of p-toluenesulphonic acid and the mixture is stirred at 25° C. for 14 h. It is washed with aqueous sodium hydrogen carbonate solution and water, dried over sodium sulphate and concentrated in vacuo, and the residue is chromatographed on a silica gel column using petroleum ether.

Workup

  1. washIt is washed with aqueous sodium hydrogen carbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customthe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-b27ce8b9bd4d4c65a32968235c771972
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

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