2-Phenylethanol → HCID 90203155, compound

HRID 927042Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15]C=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:21](O)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/[N:54]=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][N:54]=2)=[N:10][O:11][CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of [3-(4-hydroxy-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (68 mg, 0.247 mmol), phenethyl alcohol (30 μL, 0.25 mmol)) and triphenylphosphine (136 mg, 0.52 mmol) in THF (1.5 mL) at 0° C. was added diethylazodicarboxylate (100 μL, 0.55 mmol) over 1.5 h. The reaction mixture was warmed to 90° C. for 62 h and cooled to rt. Volatiles were removed under reduced pressure and the crude product was dry-loaded onto silica gel. Chromatography provided [3-(5-phenethyloxy-pyridin-2-yl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (60 mg, 64%).

Workup

temperaturecooled to rt
customVolatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-e79f925389bf443ba968f4a81ff4acda
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290465B2

Reaction notes

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