Phthalimide → N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimide

HRID 963709Notes

Reaction equation

HRID 963709 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][CH:19]([CH2:25]O)[CH2:20]2.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][CH:19]([CH2:25][N:31]1[C:30](=[O:32])[C:29]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]3[C:27]1=[O:37])[CH2:20]2

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53744579(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 70187305N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimideYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (871 mg) in tetrahydrofuran (4 ml) was added slowly to a stirred solution of (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methanol (961 mg), phthalimide (736 mg), and triphenyiphosphine (1.31 g) in tetrahydrofuran (10 ml) at room temperature and the resulting mixture was stirred at the same temperature for 24 hours. The reaction mixture was evaporated in vacuo and the residue was chromatographed (toluene) over silica gel. The eluate was evaporated in vacuo and the residue was triturated with n-hexane to afford N-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]phthalimide (888 mg) as a colorless powder. mp: 143°-144° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was chromatographed (toluene) over silica gel
  3. customThe eluate was evaporated in vacuo
  4. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-0ae3efc6dec547a68d44efb465e3d8f3
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

Loading…