Acetic Anhydride → HCID 136378652, compound

HRID 527526Notes

Reaction equation

HRID 527526 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[N:12][OH:13])[CH2:10][CH3:11].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:13][N:12]=[C:9]([C:3]1[C:4]([OH:8])=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])[CH2:10][CH3:11])(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136378651HCID 136378651, compound2×

Product 1

HCID 136378652HCID 136378652, compoundYield 30.5%

Procedure

1-(2,6-dihydroxyphenyl)-1-propanone oxime (Intermediate 29, 716 mg) was stirred in acetic anhydride (2.24 ml, 23.7 mmol) at room temperature for 1 hour. After removal of the volatiles, the residue was washed with water, filtered and dried. The crude compound was charged on a silica gel column (Biotage SP1 system) and eluted with Cyclohexane/EtOAc (from 100/0 to all 0/100) to afford the title compound (269 mg).

Workup

  1. customAfter removal of the volatiles
  2. washthe residue was washed with water
  3. filtrationfiltered
  4. customdried
  5. additionThe crude compound was charged on a silica gel column (Biotage SP1 system)
  6. washeluted with Cyclohexane/EtOAc (from 100/0 to all 0/100)

Sources & evidence

ORD record
ord-62ce0eca3bda4c52840c4cf170ea354d
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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