4-Phenoxyphenol → HCID 10113515, compound

HRID 459092Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([O:18][CH3:19])[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1.[O:20]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:19][O:18][C@@H:14]([CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]#[C:5][CH2:4][CH2:3][CH2:2][O:1][C:30]2[CH:31]=[CH:32][C:27]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:28][CH:29]=2)=[CH:12][CH:11]=1)[C:15]([OH:17])=[O:16]

Participants

Reactant 2

HCID 132544-Phenoxyphenol

HCID 69423953HCID 69423953, compound

Product 1

HCID 10113515HCID 10113515, compound

Procedure

The title compound was prepared from (2S)-3-[4-(5-hydroxy-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid (Example 21, Step A) and 4-phenoxyphenol via the standard Mitsunobu coupling-hydrolysis procedure (Standard Procedure A) to produce a white oily solid. 1H-NMR (200.15 MHz, CDCl3): δ 7.26–7.19 (m, 4H), 7.07 (d, 2H, J=8.3), 6.98–6.78 (m, 7H), 4.01 (t, 2H, J=5.9), 3.91 (dd, 1H, J=7.3, 4.3), 3.30 (s, 3H), 3.05 (dd, 1H, J=14.2, 4.3), 2.90 (dd, 1H, J=14.2, 7.5), 2.54 (t, 2H, J=6.7), 1.98 (qn, 2H, J=6.4). MS (ES) for C27H26O5[M+NH4]+: 448, [M+Na]+: 453.

Workup

customto produce a white oily solid

Sources & evidence

ORD record: ord-e76a9cd9a77d42fb9e165cf41a0c22ee
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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