Methyl iodide → HCID 59563815, compound

HRID 1020134Notes

Reaction equation

[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]1([C:17](=[N:24][CH2:25][CH:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]([O:29][CH3:30])=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:37]I>C1COCC1>[C:11]1([C:17](=[N:24][CH2:25][C:26]([CH3:37])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]([O:29][CH3:30])=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of LiHMDS in THF cooled to −78° C. was added a solution of methyl 3-(diphenylmethyleneamino)-2-phenylpropanoate (E320) in THF also cooled to approximately −78° C. This solution stirred for 30 min at −78° C., then methyl iodide was added directly and the solution was warmed to 0° C. After 3 h the solution was poured into NH4Cl(sat) and extracted with EtOAc. The combined organics were dried (Na2SO4) filtered, and evaporated. Column chromatography (SiO2, 0-15% EtOAc/Hexanes) gave pure methyl 3-(diphenylmethyleneamino)-2-methyl-2-phenylpropanoate (E321).

Workup

temperaturethe solution was warmed to 0° C
extractionextracted with EtOAc
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-cfb7882781144b5491a227671b397b6a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716310B2

Reaction notes

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