Hydrochloric Acid → HCID 15199841, compound

HRID 372117Notes

Reaction equation

HRID 372117 reaction equation
[CH2:1]1[CH2:37][O:36][C:3]([CH2:24][O:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)(/[CH:4]=[CH:5]/[C@H:6]2[C@H:13]([O:14]C(=O)C3C=CC=CC=3)[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:23])[O:10]3)[O:2]1.C(=O)([O-])[O-].[K+].[K+].CO.Cl>[Cl-].[Na+].O>[CH2:1]1[CH2:37][O:36][C:3]([CH2:24][O:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=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:23])[O:10]3)[O:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 22803347HCID 22803347, compound

Product 1

HCID 15199841HCID 15199841, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 500 mg. of (1S,5R,6R,7R)-6-[(E)-3,3-ethylenedioxy-4-(2-naphthyloxy)-1-butenyl]-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one (prepared according to Example 1[a]), 138 mg. of anhydrous potassium carbonate, and 20 ml. of methanol was stirred for 2 hours at room temperature under an argon atmosphere. The mixture was then diluted with 20 ml. of 0.1N hydrochloric acid, agitated for 10 minutes, diluted with brine, and extracted with methylene chloride. The organic phase was washed with brine, dried over magnesium sulfate, and evaporated under vacuum. The residue was recrystallized from diisopropyl ether/methylene chloride, thus obtaining 290 mg. of the title compound as colorless crystals, m.p. 159°. IR: 3600, 1770, 1630, 1600, 1510, 977 cm-1.

Workup

  1. additionA mixture of 500 mg
  2. additionThe mixture was then diluted with 20 ml
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was recrystallized from diisopropyl ether/methylene chloride
  8. customthus obtaining 290 mg

Sources & evidence

ORD record
ord-c14955898ede4d70ad0a2dbc3f1bc7e0
Source dataset
uspto-grants-1978_05
Patent number
US04088775

Reaction notes

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