HCID 57890277, compound → HCID 59263548, compound

HRID 644154Notes

Reaction equation

HRID 644154 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9](=[O:26])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)=[CH:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>C(O)C>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([CH:9]([OH:26])[CH:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 57890277HCID 57890277, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59263548HCID 59263548, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1 L 3N round-bottomed hydrogenation flask, 7-acetoxy-3-(3,4-dimethoxyphenyl)-8-methylchromen-4-one (13.9 g) and Pd/Al2O3 (2.8 g) were suspended in absolute ethanol (560 mL). Hydrogen was introduced to the system for 42 h until the reaction was complete. The reaction mixture was separated by filtration with Celite. The solvent was removed in vacuo to give a white solid which was dried overnight on a high-vacuum line yielding 7-acetoxy3-(3,4-dimethoxyphenyl)-8-methylchroman-4-ol as a mixture of cis- and trans-isomers (9.56 g, 68%). This mixture was used in the next step without any further purification.

Workup

  1. customThe reaction mixture was separated by filtration with Celite
  2. customThe solvent was removed in vacuo
  3. customto give a white solid which
  4. customwas dried overnight on a high-vacuum line

Sources & evidence

ORD record
ord-fde6baaeceb94374b6fca4878ea8829a
Source dataset
uspto-grants-2010_04
Patent number
US07700644B2

Reaction notes

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