Triphenylphosphine → 2-[(N,N-Dimethylamino)methyl]-6-(4-nitrobenzyloxy)tetralin

HRID 1242896Notes

Reaction equation

HRID 1242896 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=2)[CH2:18]1)[CH3:15].[N+:28]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35]O)=[CH:33][CH:32]=1)([O-:30])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:15][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH2:35][C:34]3[CH:37]=[CH:38][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=3)[CH:23]=2)[CH2:18]1)[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 692754-Nitrobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Product 1

HCID 219399852-[(N,N-Dimethylamino)methyl]-6-(4-nitrobenzyloxy)tetralinYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (40% toluene solution, 9.53 g) was added dropwise to THF solution (15 ml) of 2-[(N,N-dimethylamino)methyl]-6-hydroxytetralin (1.5 g), 4-nitrobenzylalcohol (3.35 g), and triphenylphosphine (5.74 g) at room temperature, which was stirred for 24 hours. The reaction mixture was concentrated, and the residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=8:1), and recrystallized (ethyl acetate-hexane) to give the titled compound (1.29 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified
  3. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-23e733a24e8a4af4934b76d98f081a89
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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