4-Hydroxybenzophenone → HCID 10160561, compound

HRID 459093Notes

Reaction equation

HRID 459093 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[C:21]1[CH:34]=[CH:33][C:24]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C@H:14]([O:18][CH3:19])[C:15]([OH:17])=[O:16])=[CH:11][CH:12]=2)=[CH:29][CH:28]=1)(=[O:26])[C:24]1[CH:33]=[CH:34][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 143474-HydroxybenzophenoneHCID 69423953HCID 69423953, compound

Product 1

HCID 10160561HCID 10160561, 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-hydroxybenzophenone via the standard Mitsunobu coupling-hydrolysis procedure (Standard Procedure A) to produce a white oily solid. 1H-NMR (200.15 MHz, CDCl3): δ 7.82–7.70 (m, 3H), 7.54–7.43 (m, 4H), 7.31–7.23 (m, 2H), 7.14 (d, 2H, J=8.1), 6.95 (d, 2H, J=8.8), 4.19 (d, 2H, J=5.9), 3.96 (dd, 1H, J=7.7, 4.4), 3.34 (s, 3H), 3.09 (dd, 1H, J=14.3, 4.4), 2.95 (dd, 1H, J=14.3, 7.7), 2.61 (t, 2H, J=7.0), 2.08 (qn, 2H, J=0.6).

Workup

  1. customto produce a white oily solid

Sources & evidence

ORD record
ord-de35b9d630e845259783fcf8ac07cb84
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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