Triphenylphosphine → 2-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxybenzyl)oxy]benzyloxy]tetralin

HRID 1242879

Reaction equation

HRID 1242879 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].[CH3:28][O:29][C:30]1[CH:45]=[CH:44][C:33]([CH2:34][O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40]O)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1.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][CH2:40][C:39]3[CH:42]=[CH:43][C:36]([O:35][CH2:34][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:45][CH:44]=4)=[CH:37][CH:38]=3)[CH:23]=2)[CH2:18]1)[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 126484214-[(4-Methoxyphenyl)methoxy]benzenemethanolHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Product 1

HCID 219400532-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxybenzyl)oxy]benzyloxy]tetralinYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (40% toluene solution, 1.91 g) was added dropwise to THF solution (6 ml) of 2-[(N,N-dimethylamino)methyl]-6-hydroxytetralin (300 mg), 4-[(4-methoxybenzyl)oxy]benzylalcohol (1.07 g) and triphenylphosphine (1.15 g) at room temperature, which was stirred for 12 hours. The reaction mixture was concentrated, and the residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=10:1), and recrystallized (ethyl acetate-hexane) to give the titled compound (260 mg).

Workup

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

Sources & evidence

ORD record
ord-037b1f8e563c4a369842696cc76cff45
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Linked notes

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