4-Hydroxybiphenyl → HCID 10112472, compound

HRID 459091Notes

Reaction equation

HRID 459091 reaction equation
C([O:3][C:4](=[O:21])[C@@H:5]([O:19][CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:9][CH:8]=1)C.[C:22]1([C:28]2[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:27]=[CH:26][C:25]([O:18][CH2:17][CH2:16][CH2:15][C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:19][CH3:20])[C:4]([OH:3])=[O:21])=[CH:12][CH:11]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 71034-HydroxybiphenylHCID 58822996HCID 58822996, compound

Product 1

HCID 10112472HCID 10112472, compound

Procedure

The title compound was prepared from (2S)-3-[4-(5-hydroxy-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester and 4-phenylphenol via the standard Mitsunobu coupling-hydrolysis procedure (Standard Procedure A) to produce a white oily solid. 1H-NMR (200.15 MHz, CDCl3): δ 7.56–7.28 (m, 9H), 7.15 (d, 2H, J=8.4), 6.98 (d, 2H, J=8.8), 4.15 (t, 2H, J=6.2), 3.97 (dd, 1H, J=7.7, 4.4), 3.36 (s, 3H), 3.11 (dd, 1H, J=14.3, 4.4), 2.97 (dd, 1H, J=14.3, 7.7), 2.62 (t, 2H, J=7.0), 2.08 (qn, 2H, J=6.6).

Workup

  1. customto produce a white oily solid

Sources & evidence

ORD record
ord-452ebda1d15e423e8326d0858dc275d2
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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