Potassium Hydroxide → 5-Amino-2-butyl-4,6-difluoro-2-(3-oxohexyl)-1-indanone

HRID 1372526Notes

Reaction equation

HRID 1372526 reaction equation
[NH2:1][C:2]1[C:3]([F:17])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[CH:6]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]2.[OH-:18].[K+].C=C[C@@H]1[C@@H]2C[C@H]([C@@H](O)C3C4C(=CC=CC=4)N=CC=3)[N+](CC3C=CC(C(F)(F)F)=CC=3)(CC2)C1.[Br-].[CH:54]([C:56]([CH2:58][CH2:59][CH3:60])=[O:57])=[CH2:55]>C1(C)C=CC=CC=1.C(Cl)Cl>[NH2:1][C:2]1[C:3]([F:17])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:18])[C:6]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:55][CH2:54][C:56](=[O:57])[CH2:58][CH2:59][CH3:60])[CH2:5]2

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 153951-Hexen-3-oneHCID 11421253HCID 11421253, compoundHCID 210720025-Amino-2-butyl-4,6-difluoro-1-indanone

Product 1

HCID 210720035-Amino-2-butyl-4,6-difluoro-2-(3-oxohexyl)-1-indanone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-2-butyl-4,6-difluoro-1-indanone (0.25 g, 1.05 mmol) in toluene (5.5 mL) was treated with potassium hydroxide (0.1 g, 40% w/w), N-[4-(trifluoromethyl)benzy]cinchoninium bromide (0.112 g, 0.21 mmol), and propyl vinyl ketone (0.154 g, 1.57 mmol). The resulting solution was stirred under a nitrogen atmosphere for 2 hours. After being diluted with CH2Cl2, the mixture was filtered through a pad of silica gel and rinsed with EtOAc. The filtrate was evaporated under vacuum to afford crude 5-amino-2-butyl-4,6-difluoro-2-(3-oxohexyl)-1-indanone.

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. washrinsed with EtOAc
  3. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-67dbdc916ac9477daab2b0bf929cf0fa
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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