Triethylamine → (E)-3-(4-fluoro-3-methoxyphenyl)-2-(4-isopropoxyphenyl)acryloyl azide

HRID 1852090Notes

Reaction equation

HRID 1852090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)/[C:10](O)=[O:11])=[CH:4][C:3]=1[O:23][CH3:24].P([N:41]=[N+:42]=[N-:43])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.CCN(CC)CC>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)/[C:10]([N:41]=[N+:42]=[N-:43])=[O:11])=[CH:4][C:3]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 70978345(E)-3-(4-fluoro-3-methoxyphenyl)-2-(4-isopropoxyphenyl)acrylic acid

Product 1

HCID 89156424(E)-3-(4-fluoro-3-methoxyphenyl)-2-(4-isopropoxyphenyl)acryloyl azideYield 51.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(E)-3-(4-fluoro-3-methoxyphenyl)-2-(4-isopropoxyphenyl)acrylic acid (4.38 g, 13.26 mmol), (PhO)2PON3 (2.71 mL, 12.60 mmol), and Et3N (3.70 mL, 26.5 mmol) were dissolved in benzene and stirred for 16 h. The solution was concentrated under vacuum and the residue was purified by silica gel chromatography using 20% EtOAc/Hexanes to give (E)-3-(4-fluoro-3-methoxyphenyl)-2-(4-isopropoxyphenyl)acryloyl azide (2.3 g, 49% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.80 (s, 1H), 7.16-7.11 (m, 2H), 6.97-6.92 (m, 2H), 6.84-6.78 (m, 1H), 6.63-6.53 (m, 2H), 4.63-4.54 (m, 1H), 3.49 (s, 3H), 1.38-1.35 (m, 6H).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4089f80a0e6845a3bb446042d3b86021
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…