Phthalimide → HCID 131730024, compound

HRID 2065949Notes

Reaction equation

HRID 2065949 reaction equation
COC(O[CH:6]([CH3:14])/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>C(Cl)Cl.[Pd].CCCCCCC>[C:15]1(=[O:25])[N:19]([CH:6]([CH3:14])/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 58489101HCID 58489101, compound

Product 1

HCID 131730024HCID 131730024, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Reaction of 1 (rac-Ethyl (2E)-4-(methoxycarbonyloxy)pent-2-enoate) (104 mg, 0.50 mmol) with phthalimide (147 mg, 1.0 mmol), Cs2CO3 (40.7 mg, 0.125 mmol) and 5 mol % [Pd] in CH2Cl2 (10 ml) at room temperature according to Example 2. Flash chromatography (AcOEt:heptane fraction 25:75) yields 16 (rac-Ethyl (2E)-4-phthalimidopent-2-enoate) (124 mg, 90%) as a yellowish solid.

Sources & evidence

ORD record
ord-61096b886f1940abbe4726a9fcecb8e4
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

Loading…