6-Hydroxyflavanone → 6-(2-Azidoethoxy)-2-phenylchroman-4-one

HRID 31260Notes

Reaction equation

[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:10]2)=[N+:2]=[N-:3].[OH:23]C1C=C2C(=CC=1)OC(C1C=CC=CC=1)CC2=O>>[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][C:10]2=[O:23])=[N+:2]=[N-:3]

Participants

Reactant 2

HCID 27345806-Hydroxyflavanone

HCID 179785706-(2-Azidoethoxy)-2-phenylchroman

Product 1

HCID 179785726-(2-Azidoethoxy)-2-phenylchroman-4-one

Procedure

6-(2-Azidoethoxy)-2-phenylchroman-4-one was prepared as described for 6-(2-azidoethoxy)-2-phenylchroman in example 4(a) starting from 1.0 g of 6-hydroxy-flavanone. 1H NMR (400 MHz, CD3OD) δ: 7.53-7.51 (m, 2H), 7.44-7.35 (m, 4H), 7.22 (dd, 1H, J 9.0, 3.1 Hz), 7.04 (d, 1H, J 9.0 Hz), 5.51 (dd, 1H, J 13.1, 3.0 Hz), 4.17 (t, 2H, J 4.9 Hz), 3.60 (t, 2H, J 4.9 Hz), 3.11 (dd, 1H, J −16.9, 13.1 Hz), 2.85 (dd, 1H, J −16.9, 3.0 Hz).

Sources & evidence

ORD record: ord-904f73c6e0444794a1533c01f7b605aa
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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