Ammonium Chloride → 1-(4-Iodo-phenyl)-5-methoxy-pent-4-ene-1,3-dione

HRID 19614

Reaction equation

C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][O:12][CH:13]=[CH:14][C:15](=[O:17])[CH3:16].[I:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[I:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](=[O:24])[CH2:16][C:15](=[O:17])[CH:14]=[CH:13][O:12][CH3:11])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -70 °C

Procedure

In a 1 ltr flask is cooled a solution of lithium hexamethyldisilazide (50 ml, 1.5 M) in THF (250 ml) to −75° C. During a period of 1 h is added 4-methoxy-but-3-en-2-one (6 ml). The mixture is stirred for 1 h at −70° C. A solution of 4-iodobenzoylchloride (7.2 g) in THF (250 ml) is added to the above mixture during 1 h at −70° C. The resulting mixture is slowly heated to ambient temperature and stirred for 1 h. Subsequently, the mixture is added to a cold aqueous solution of ammonium chloride and the resulting suspension is extracted with ethyl acetate. The organic phase is extracted twice with an aqueous solution of ammonium chloride, dried over sodium sulfate and evaporated. The crude oily product is transferred to the next step without any further purification.

Workup

temperatureThe resulting mixture is slowly heated to ambient temperature
stirringstirred for 1 h
extractionthe resulting suspension is extracted with ethyl acetate
extractionThe organic phase is extracted twice with an aqueous solution of ammonium chloride
dry with materialdried over sodium sulfate
customevaporated
customThe crude oily product is transferred to the next step without any further purification

Sources & evidence

ORD record: ord-da88ff71f72f4a34b33a1f2096cda387
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745446B2

Linked notes

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