Toluene → HCID 59331259, compound

HRID 1881952Notes

Reaction equation

[CH:1]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)C(=O)CC(=O)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[C-:25].[C:32]1(C)[CH:37]=CC=C[CH:33]=1>>[CH:1]1([CH2:6][CH:7]([C:25]2[NH:24][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:32]([CH3:37])[CH:33]=2)[C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 1140Toluene

HCID 533707Ethyl isocyanoacetate

HCID 59331615HCID 59331615, compound

Product 1

HCID 59331259HCID 59331259, compoundYield 43%

Conditions

Temperature: 80 °C

Procedure

To a solution (5 mL) of 6-cyclopentyl-5-[4-(methylsulfonyl)phenyl]hexane-2,4-dione (1.60 g) in toluene were added ethyl isocyanoacetate (0.29 g) and dodecacarbonyltetrarhodium(0) complex (55 mg), and the mixture was stirred under argon atmosphere at 80° C. overnight. After cooling to room temperature, the reaction mixture was concentrated, and the residue was subjected to NH silica gel column chromatography, and the title compound (0.44 g, yield 43%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 404 (MH+).

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record: ord-c338aa3806a34b2fb790de8c6c5c8782
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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