Ethyl Acetate → HCID 68779597, compound

HRID 2263369Notes

Reaction equation

C[O:2][C:3]([C:5]1[O:9][C:8]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:7][C:6]=1[CH2:20][O:21][CH3:22])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>O1CCCC1>[CH3:22][O:21][CH2:20][C:6]1[N:7]=[C:8]([CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[O:9][C:5]=1[CH2:3][OH:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1.10 g 4-Methoxymethyl-2-[2-(4-methoxy-phenyl)-vinyl]-oxazole-5-carboxylic acid methyl ester were dissolved in 15 ml tetrahydrofuran and added to a ice cooled solution of 137 mg lithium aluminium hydride in 7 ml tetrahydrofuran. The reaction mixture was stirred at 0° C. for one hour. Then 50 ml ethyl acetate and 20 ml saturated NH4Cl solution were added. The precipitate was filtered off through a celite pad and washed with ethyl acetate. The organic layer of the filtrate was separated. The aqueous layer of the filtrate was extracted two times with portions of 100 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the residue purified by RP-HPLC to obtain to 420 mg {4-methoxymethyl-2-[2-(4-methoxy-phenyl)-vinyl]-oxazol-5-yl}-methanol as an oil.

Workup

filtrationThe precipitate was filtered off through a celite pad
washwashed with ethyl acetate
customThe organic layer of the filtrate was separated
extractionThe aqueous layer of the filtrate was extracted two times with portions of 100 ml ethyl acetate
dry with materialThe combined organic layers were dried over MgSO4
customThe solvent was removed in vacuo
customthe residue purified by RP-HPLC

Sources & evidence

ORD record: ord-83eace48dbc2472a911a4eb3a6f48f3e
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851493B2

Reaction notes

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