Ethyl acetate hexane → HCID 57949529, compound

HRID 2427758Notes

Reaction equation

HRID 2427758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]#[CH:24])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH2:7]2.[H][H].CCCCCC.C(OCC)(=O)C>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][CH3:24])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 86635680HCID 86635680, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57949529HCID 57949529, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-ethynyl-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.035 g, 0.1 mmol) and 10% palladium on carbon (20 mg) in ethanol (25 mL) was reduced under 45 p.s.i. hydrogen. Workup and silica gel column chromatography using combinations 3:1 hexane-ethyl acetate afforded 7-chloro-5-ethyl-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.015 g, 43%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.23 (t, 3H), 2.69 (q, 2H), 4.20 (s, 2H), 4.81 (s, 2H), 7.09 (s, 1H), 7.24 (d, 1H), 7.42 (d, 2H), 7.59 (d, 2H). GC-MS: m/z 353 (M)+, 334 (M−29)+, 284 (M−50)+.

Sources & evidence

ORD record
ord-1de1a2536e8f44eeaf7972c95f5d46df
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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