Hydrochloric Acid → 3-(2-Anilinothiazol-4-yl)allyl alcohol

HRID 2107266Notes

Reaction equation

CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[NH:17]([C:24]1[S:25][CH:26]=[C:27]([CH:29]=[CH:30][C:31](OCC)=[O:32])[N:28]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCCC1.CO>[NH:17]([C:24]1[S:25][CH:26]=[C:27]([CH:29]=[CH:30][CH2:31][OH:32])[N:28]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: -50 °C

Procedure

58 ml of a 1M hexane solution of diisobutyl aluminum hydride was added dropwise at -60° C. to a solution of 4 g of ethyl 3-(2-anilinothiazol-4-yl)acrylate (prepared by the procedure described in Preparation 48) in 40 ml of tetrahydrofuran. The resulting mixture was stirred at -50° C. for 2 hours, then the excess of the reducing reagent was decomposed with 90% aqueous methanol. The mixture was then neutralized with 3N hydrochloric acid and extracted with ethyl acetate. After the extract was dried over anhydrous sodium sulfate. the solvent was evaporated off under reduced pressure, giving crude 3-(2-anilinothiazol-4-yl)allyl alcohol.

Workup

customprepared by the procedure
extractionextracted with ethyl acetate
dry with materialAfter the extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-b475f0aec9064786b9d13a3a4ce47621
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933355

Reaction notes

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