1,2-Bis(1,3-benzodioxol-5-yl)-2-hydroxyethanone → HCID 10014790, compound

HRID 339646Notes

Reaction equation

HRID 339646 reaction equation
C1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]([CH:12]([C:14]3[CH:19]=[CH:18][C:17]4[O:20]C[O:22][C:16]=4[CH:15]=3)O)=O)=[CH:4][C:3]=2[O:2]1>CO.[OH-].[OH-].[Pd+2]>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:12][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:22])[CH:15]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 1

HCID 977861,2-Bis(1,3-benzodioxol-5-yl)-2-hydroxyethanone

Product 1

HCID 10014790HCID 10014790, compoundYield 74,899.797%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of the tetrahydroxybenzil (see Example 1) (70 mg) in methanol (10 ml) with palladium hydroxide on carbon (20%, 10 mg) was stirred under an atmosphere of hydrogen for 2 hours. The mixture was filtered through Celite, and the solvents removed in vacuo to give an orange gum. Separation by column chromatography over silica gel eluting with 20% ethyl acetate in dichloromethane gave DC-0004 as an off white gum (43 g, 68%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvents removed in vacuo
  3. customto give an orange gum
  4. customSeparation by column chromatography over silica gel eluting with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-5354b5a64a2848e4a0580f9a1abf889d
Source dataset
uspto-grants-2014_11
Patent number
US08895554B2

Reaction notes

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