p-Toluenesulfonic acid → HCID 22803348, compound

HRID 372118Notes

Reaction equation

HRID 372118 reaction equation
[CH2:1]1[CH2:29][O:28][C:3]([CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(/[CH:4]=[CH:5]/[C@H:6]2[C@H:13]([OH:14])[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[CH2:1]1[CH2:29][O:28][C:3]([CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(/[CH:4]=[CH:5]/[C@H:6]2[C@H:13]([O:14][CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][O:30]3)[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 15199841HCID 15199841, compound

Product 1

HCID 22803348HCID 22803348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

190 mg. of (1S,5R,6R,7R)-6-[(E)-3,3-ethylenedioxy-4-(2-naphthyloxy)-1-butenyl]-7-hydroxy-2-oxabicyclo[3,3,0]octan-3-one (prepared according to Example 5[a]), 0.2 ml. of freshly distilled dihydropyran, and 1.4 mg. of p-toluenesulfonic acid in 5 ml. of absolute methylene chloride were stirred for 30 minutes at ice bath temperature under argon. After dilution with methylene chloride, the mixture was shaken successively with sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated under vacuum. The residue was recrystallized from diisopropyl ether/methylene chloride, thus obtaining 204 mg. of the title compound as colorless crystals, m.p. 113°. IR: 1770, 1630, 1600, 975 cm-1.

Workup

  1. dry with materialdried over magnesium sulfate
  2. customevaporated under vacuum
  3. customThe residue was recrystallized from diisopropyl ether/methylene chloride
  4. customthus obtaining 204 mg

Sources & evidence

ORD record
ord-55e6ad93ca714a7e991ceb49738370fd
Source dataset
uspto-grants-1978_05
Patent number
US04088775

Reaction notes

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