Methanol → HCID 86729312, compound

HRID 1474611Notes

Reaction equation

HRID 1474611 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][CH:6]1Br)(=[O:3])[CH3:2].[CH3:35][OH:36]>>[C:16]([O:15][C@@H:9]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@@H:6]([O:36][CH3:35])[O:7][C@H:8]1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[CH:20]=1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 887MethanolHCID 86729310HCID 86729310, compound

Product 1

HCID 86729312HCID 86729312, compoundYield 65%

Conditions

Temperature
60 °C

Procedure

To a solution of (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (2.02 g, 3.62 mmol) in methanol (15 mL) was added ZnO (294.5 mg, 3.62 mmol) at 60° C. The reaction mixture was stirred at 60° C. for 1 h. After completion of reaction, as confirmed by TLC, reaction mixture was passed through sintered funnel to remove the solids. The filterate was evaporated in vacuo and the residue obtained was purified by column chromatography (silica gel, 2:8 Acetone:Pet. Ether) to afford title compound (1.1 g, 65%)

Workup

  1. customAfter completion of reaction
  2. customas confirmed by TLC, reaction mixture
  3. customwas passed through sintered funnel
  4. customto remove the solids
  5. customThe filterate was evaporated in vacuo
  6. customthe residue obtained
  7. customwas purified by column chromatography (silica gel, 2:8 Acetone:Pet. Ether)

Sources & evidence

ORD record
ord-bb93ac0c46b04cec94a7daf38ef32c0e
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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