Isovaleryl chloride → HCID 89627239, compound

HRID 2203253Notes

Reaction equation

HRID 2203253 reaction equation
[CH3:1][C:2]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:3]=1[C:4]([C:6]1[CH:18]=[C:17]2[C:9]([N:10]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=3)[C:11]3[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12)=[O:5].[C:38](Cl)(=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:10]2[C:9]3[C:17](=[CH:18][C:6]([C:4](=[O:5])[C:3]4[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:2]=4[CH3:1])=[C:7]4[CH:31]=[CH:30][CH:29]=[CH:28][C:8]4=3)[C:16]3[C:11]2=[CH:12][CH:13]=[C:14]([C:38](=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41])[CH:15]=3)=[CH:24][CH:23]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 89615123HCID 89615123, compound

Product 1

HCID 89627239HCID 89627239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-{4-[5-(2,4,6-trimethyl-benzoyl)-benzo[a]carbazol-11-yl]-phenyl}-ethanone (383 mg, 0.795 mmol) in CH2Cl2 (10 mL) are added isovaleroyl chloride (120 mg, 0.995 mmol) and AlCl3 (350 mg, 2.62 mmol) at 0° C. After stirring for 2 hours, the reaction mixture is poured into ice-water, and the crude product is extracted with CH2Cl2. The organic layer is washed with water and brine, dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain an off-white solid (345 mg; 76%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 1.02 (d), 2.22 (s), 2.34 (m), 2.43 (s), 2.78 (s), 2.94 (d), 7.00 (s), 7.14 (d), 7.33 (t), 7.48 (d), 7.64-7.68 (m), 7.98 (d), 8.31 (d), 8.43 (s), 8.67 (s), 9.47 (d).

Workup

  1. extractionthe crude product is extracted with CH2Cl2
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2
  6. customto obtain an off-white solid (345 mg; 76%)

Sources & evidence

ORD record
ord-654f1c5b2e3d4f9293760d041f3d37b5
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

Loading…