Hydrochloric Acid → N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyisoindoline

HRID 850494Notes

Reaction equation

HRID 850494 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:20](=O)[C:19]3=[CH:22][C:23](OCCCCC)=[CH:24][CH:25]=[C:18]3[C:17]2=O)=[CH:10][CH:9]=1.Cl>C1COCC1>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[CH2:20][C:19]3[C:18](=[CH:25][CH:24]=[CH:23][C:22]=3[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:17]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19363249HCID 19363249, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19363389N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyisoindolineYield 188.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of LAH (40 mg, 1.1 mmol) in THF (1 ml) was added to a solution of N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyphthalimide (208 mg, 0.59 mmol) in THF (1 ml) at 0° C. The mixture was stirred at room temperature for 3.5 hours. This reaction mixture was poured into a 3N aqueous hydrochloric acid solution (20 ml). The mixture was extracted with ethyl acetate (20 ml×3), and washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (30 ml). The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered of, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=30/1) to give N-2-(4-hydroxyphenyl)ethyl-4-pentyloxyisoindoline (181 mg, 94%) as colorless crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (20 ml×3)
  2. washwashed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (30 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered of, and the filtrate
  5. concentrationwas concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-8a1b81e3178f4bf8b82f2dcc9edb29b6
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

Loading…