Water → HCID 70360330, compound

HRID 1073458Notes

Reaction equation

HRID 1073458 reaction equation
C([O:4][CH2:5][C@:6]1([O:28][C@H:27]([CH2:29][OH:30])[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:9]1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][OH:8])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[OH:4][CH2:5][C:6]1([O:28][C@H:27]([CH2:29][OH:30])[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:9]1[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 70360298HCID 70360298, compound

Product 1

HCID 70360330HCID 70360330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.7 g portion of 2-C-[(acetyloxy)methyl]-2,5-anhydro-3,4-bis-O-(phenylmethyl)-D-glucitol, 1,6-diacetate was treated with 1.6 g of potassium carbonate, 10 ml of water and 8.5 ml of methanol and the mixture heated at reflux for 40 minutes and then evaporated. The residue was taken up in ether/water. The water layer was extracted twice with ether. All ether layers were combined, washed with brine, dried and evaporated. The residual oil was flash chromatographed, eluting with 4% methanol in dichloromethane, giving 1.0 g of the desired compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 40 minutes
  3. customevaporated
  4. extractionThe water layer was extracted twice with ether
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customchromatographed
  9. washeluting with 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-a80853a09d574f128752c67d2845d42d
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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