2-Tridecanone → N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-tetradecanamide

HRID 1198038Notes

Reaction equation

HRID 1198038 reaction equation
[CH3:1][C:2](=[O:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:19]=1[N:27]=[C:28]=[O:29])([CH3:17])[CH3:16].C([N-]C(C)C)(C)C.[Li+]>>[CH3:17][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:25])[CH3:26])[C:19]=1[NH:27][C:28](=[O:29])[CH2:1][C:2](=[O:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:16]

Participants

4

Reactant 3

HCID 116222-TridecanoneHCID 922592,6-Diisopropylphenyl isocyanateHCID 2724682Lithium diisopropylamide

Product 1

HCID 10476188N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-tetradecanamideYield 65%

Procedure

The title compound was prepared from 2-tridecanone (10.0 g, 0.050 mol), 2,6-diisopropylphenyl isocyanate (10.16 g, 0.050 mol) and lithium diisopropylamide (0.050 mol) using the procedure described in Example 1. Purification by flash chromatography (silica gel, 15% EtOAc/hexane) yielded 13.14 g (0.032 mol, 65%) of the desired product.

Workup

  1. customPurification by flash chromatography (silica gel, 15% EtOAc/hexane)

Sources & evidence

ORD record
ord-145ba8a02c4c410d8e4502e36c019625
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

Loading…