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

HRID 1198050Notes

Reaction equation

[CH3:1][C:2](=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:28])[CH3:27])[C:21]=1[N:29]=[C:30]=[O:31])([CH3:19])[CH3:18].C([N-]C(C)C)(C)C.[Li+]>>[CH3:19][CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:27])[CH3:28])[C:21]=1[NH:29][C:30](=[O:31])[CH2:1][C:2](=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:18]

Participants

Reactant 3

HCID 613032-Pentadecanone

HCID 922592,6-Diisopropylphenyl isocyanate

HCID 2724682Lithium diisopropylamide

Product 1

HCID 9980090N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide

Procedure

The title compound was prepared from 2-pentadecanone (3.0 g, 0.013 mol), 2,6-diisopropylphenyl isocyanate (2.64 g, 0.013 mol), and lithium diisopropylamide (0.013 mol) using the procedure described in Example 1. Purification by flash chromatography (silica gel, 15% EtOAc/hexane) yielded 1.92 g (0.004, 34%) of the desired product.

Workup

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

Sources & evidence

ORD record: ord-7c236d1f04934887a673b1afa88c474b
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278326

Reaction notes

Loading…