Ethanone, 1-[4-(1,1-dimethylethyl)phenyl]-, oxime → {4-[3-(4-tert-Butyl-benzylideneaminooxy)-propoxy]-phenyl}-acetic acid methyl ester

HRID 29642Notes

Reaction equation

HRID 29642 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:13][OH:14])C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17](=[O:30])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28]Br)=[CH:21][CH:20]=1>>[CH3:15][O:16][C:17](=[O:30])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:14][N:13]=[CH:11][C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 842752Ethanone, 1-[4-(1,1-dimethylethyl)phenyl]-, oximeHCID 10803177Methyl 2-[4-(3-bromopropoxy)phenyl]acetate

Product 1

HCID 86597382{4-[3-(4-tert-Butyl-benzylideneaminooxy)-propoxy]-phenyl}-acetic acid methyl ester

Procedure

{4-[3-(4-tert-Butyl-benzylideneaminooxy)-propoxy]-phenyl}-acetic acid methyl ester was prepared from 1-(4-tert-butyl-phenyl)-ethanone oxime and [4-(3-bromo-propoxy)-phenyl]-acetic acid methyl ester using a procedure similar to step 2 of example 1. It was used crude in the subsequent reaction. 1H NMR (300 MHz, CDCl3); δ 8.07 (s, 1H), 7.52 (d, 2H), 7.40 (d, 2H), 7.20 (d, 2H), 6.88 (d, 2H), 4.35 (t, 2H), 4.10 (t, 2H), 3.70 (s, 3H), 3.58 (s, 2H), 2.21 (m, 2H), 1.34 (s, 9H).

Workup

  1. customin the subsequent reaction

Sources & evidence

ORD record
ord-e6a6c89936f543c9a4b865816ffc2c0e
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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