N-{4-[4-(2-Hydroxyethyloxy)phenyl]but-3-yn-1-yl}phthalimide → N-{4-[4-(2-Hydroxyethyloxy)phenyl]butyl}phthalimide

HRID 25140Notes

Reaction equation

HRID 25140 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH2:13][CH2:14][N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[CH:7][CH:6]=1.[H][H]>CO.C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]2[C:16](=[O:25])[C:17]3=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]3[C:19]2=[O:20])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 22566174N-{4-[4-(2-Hydroxyethyloxy)phenyl]but-3-yn-1-yl}phthalimideHCID 178418361HCID 178418361, compound

Product 1

HCID 22566183N-{4-[4-(2-Hydroxyethyloxy)phenyl]butyl}phthalimideYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 113 (1.7 g, 5.1 mmol) in a mixture of methanol/ethyl acetate (80 and 10 mL correspondingly) was placed in a 0.5 L Parr flask and palladium on carbon (1.1 g, 5% wet. Pd/C) was added. The reaction mixture was shaken at 50 psi of hydrogen pressure at room temperature overnight. After this time, the mixture was filtered through a silica gel pad and the solvent was removed at reduced pressure to give crude 114 (1.2 g) as a brown oil. The crude 114 was used in the next step without further purification.

Workup

  1. additionwas added
  2. filtrationAfter this time, the mixture was filtered through a silica gel pad
  3. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-b451575aff80487bbe23f35b2b439893
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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