Acetic Anhydride → HCID 24785288, compound

HRID 1717507Notes

Reaction equation

HRID 1717507 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:7]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:6]([N:8]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[C:35](=[O:37])[CH3:36])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67103694HCID 67103694, compound

Product 1

HCID 24785288HCID 24785288, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.0 g (10.7 mmol) crude 1c in 50 ml ml pyridine was added 4.37 g (42.8 mmol) acetic acid anhydride. The reaction mixture was stirred over night and poured into ice-cold ethyl acetate. The organic phase was washed with water and brine and were dried with magnesium sulfate. The crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:8→1:4). The desired product 1d was obtained in 84% yield (4.5 g, 8.9 mmol).

Workup

  1. additionpoured into ice-cold ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialwere dried with magnesium sulfate
  4. customThe crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:8→1:4)

Sources & evidence

ORD record
ord-851924fa70cf437298f15844120386c9
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

Loading…