2-Phenylethanol → HCID 51352347, compound

HRID 1528773Notes

Reaction equation

[H-].[Na+].C([O:5][C:6]([C:8]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:27][N:26]=[C:25]([CH3:28])[C:24]=4[CH2:29]Br)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)=[O:7])C.[CH2:31]([OH:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH3:28][C:25]1[C:24]([CH2:29][O:39][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:23]([C:20]2[CH:19]=[CH:18][C:17]([C:14]3[CH:13]=[CH:12][C:11]([C:8]4([C:6]([OH:5])=[O:7])[CH2:10][CH2:9]4)=[CH:16][CH:15]=3)=[CH:22][CH:21]=2)[O:27][N:26]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Sodium hydride (60% in mineral oil, 0.027 g, 0.68 mmol) was added to a solution of 1-[4′-(4-bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.200 g, 0.45 mmol) and phenethyl alcohol (0.06 mL, 0.45 mmol) in DMF (5 mL). The reaction was stirred at 55° C. overnight, then partitioned between EtOAc and H2O and acidified with 1 N aqueous HCl. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound.

Workup

custompartitioned between EtOAc and H2O
extractionThe aqueous layer was extracted with EtOAc
dry with materialthe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-5d16af5c0591468d9c6f11db47904ff6
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090573B2

Reaction notes

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