N-Carbethoxyphthalimide → 5-Phthalimido-1-pentanol

HRID 2395088Notes

Reaction equation

HRID 2395088 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C(N1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])(OCC)=O>C1C=CC=CC=1>[C:14]1(=[O:23])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]12

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 756345-Aminopentan-1-ol

Product 1

HCID 5948445-Phthalimido-1-pentanolYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 mL) was added N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and the solution was stirred at room temperature for 5 h). The solvents were removed under reduced pressure to yield a yellow oil. Purification by flash column chromatography using 25% ethyl acetate in petroleum ether yielded the target compound as a clear colorless oil (9.6 mg, 84%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customto yield a yellow oil
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-10c2a8c8187d4844bf840506d445aecd
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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