p-Toluenesulfonic acid → HCID 19011014, compound

HRID 1741963Notes

Reaction equation

HRID 1741963 reaction equation
CC1(C)[O:19][CH:5]2[CH:6]3[CH2:11][O:10][CH:9]([OH:12])[CH:8]=[C:7]3[CH2:13][CH:14]([O:15][CH2:16][O:17][CH3:18])[CH:4]2[O:3]1.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[CH3:18][O:17][CH2:16][O:15][CH:14]1[CH2:13][C:7]2=[CH:8][CH:9]([O:12][CH3:21])[O:10][CH2:11][CH:6]2[CH:5]([OH:19])[CH:4]1[OH:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 19010982HCID 19010982, compound

Product 1

HCID 19011014HCID 19011014, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,5,6,7,8,8a-Hexahydro-7,8-(dimethylmethylenedioxy)-6-methoxymethoxy-3H-2-benzopyran-3-ol (3.8 mg) was dissolved in 0.6 ml of dry methanol, and a catalytic amount of p-toluenesulfonic acid was added at room temperature. After the mixture was stirred at room temperature for 2 hours, triethylamine was added, and concentrated with water cooling under reduced pressure. The obtained residue was purified through a short silica gel column to provide 1.3 mg of 1,5,6,7,8,8a-hexahydro-6-methoxymethoxy-3-methoxy-3H-2-benzopyran-7,8-diol having the following properties (yield 68%).

Workup

  1. concentrationconcentrated with water cooling under reduced pressure
  2. customThe obtained residue was purified through a short silica gel column

Sources & evidence

ORD record
ord-3f0a2b9486e74f76be7a03232ba74bf8
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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