Methyl vinyl ketone → 5-Amino-2-butyl-4-chloro-6-fluoro-2-(3-oxobutyl)-1-indanone

HRID 1372504Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH:6]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]2.C[O-:19].[Na+].[CH:21]([C:23]([CH3:25])=O)=[CH2:22]>CO>[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[C:6]([CH2:22][CH2:21][CH2:23][CH3:25])([CH2:13][CH2:14][C:15](=[O:19])[CH3:16])[CH2:5]2

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 5-amino-2-butyl-4-chloro-6-fluoro-1-indanone (2.705 g, 10.6 mmol) in methanol (17 mL) was treated with sodium methoxide (0.5M solution in MeOH, 4.2 mL, 2.1 mmol) and methyl vinyl ketone (1.3 mL, 15.75 mmol). The resulting solution was stirred under a nitrogen atmosphere and heated in an oil bath at 45° C. for 21 hours. After cooling to room temperature, the mixture was filtered through a pad of silica gel and the filtrate was evaporated under vacuum to afford crude 5-amino-2-butyl-4-chloro-6-fluoro-2-(3-oxobutyl)-1-indanone.

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through a pad of silica gel
customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record: ord-21f9603f4589458d9685df8afca79c10
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157604B2

Reaction notes

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