Acetic Anhydride → HCID 18666454, compound

HRID 355348Notes

Reaction equation

HRID 355348 reaction equation
[C@@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=2[C:20](=[O:39])[CH2:21][CH2:22][C:23]2[CH:31]=[C:30]3[C:26]([CH2:27][CH2:28][CH:29]3[O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)=[CH:25][CH:24]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(O[C:44](=[O:46])[CH3:45])(=O)C>N1C=CC=CC=1>[C:8]([O:3][C@@H:2]1[C@@H:4]([O:5][C:13](=[O:12])[CH3:14])[C@H:6]([O:7][C:4](=[O:5])[CH3:6])[C@@H:8]([CH2:10][O:11][C:2](=[O:3])[CH3:1])[O:9][C@H:1]1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:44](=[O:46])[CH3:45])[C:14]=1[C:20](=[O:39])[CH2:21][CH2:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][CH2:28][CH:29]2[O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)=[CH:25][CH:24]=1)(=[O:9])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10602616HCID 10602616, compound

Product 1

HCID 18666454HCID 18666454, compoundYield 178.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2'-(β-D-Glucopyranosyloxy)-6'-hydroxy-3-(1-tetrahydropyranyloxyindan-6-yl)propiophenone (1160 mg) is dissolved in pyridine (10 ml), and thereto is added acetic anhydride (1.63 g), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the pyridine, and the residue is dissolved in ethyl acetate, washed with water, dried, and evaporated to remove the solvent to give 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(1-tetrahydropyranyloxyindan-6-yl)propiophenone (1438 mg). This product is dissolved in a mixture of acetic acid (20 ml), tetrahydrofuran (10 ml) and water (5 ml), and the mixture is stirred. The organic layer is collected, washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/acetone) to give 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(1-hydroxyindan-6-yl)propiophenone (1071 mg).

Workup

  1. customThe mixture is evaporated
  2. customto remove the pyridine
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto remove the solvent

Sources & evidence

ORD record
ord-05c741de601d4bdfb7ad018233dcfe29
Source dataset
uspto-grants-1998_11
Patent number
US05830873

Reaction notes

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