Ethyl acetate hexane → HCID 57949743, compound

HRID 2427762Notes

Reaction equation

HRID 2427762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]#[C:25][CH3:26])[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]([O:19][C:20]([F:23])([F:22])[F:21])=[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]([CH2:24][CH2:25][CH3:26])[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]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 67252622HCID 67252622, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57949743HCID 57949743, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-propynyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.082 g, 0.19 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-propyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.050 g, 69%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.94 (t, 3H), 1.64 (m, 2H), 2.63 (t, 2H), 4.20 (s, 2H), 4.78 (s, 2H), 7.09 (s, 1H), 7.14-7.38 (m, 5H). GC-MS: m/z 383 (M)+, 354 (M−29)+.

Sources & evidence

ORD record
ord-9530efa8fab54b8abee90c6ecf23fdb5
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…