Methyl iodide → HCID 3642305, compound

HRID 461744Notes

Reaction equation

[CH:1]([N-]C(C)C)(C)C.[Li+].O1CCCC1.[C:14]1([C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=2)=[O:20])[S:18][CH:17]=[CH:16][CH:15]=1.CI>CN(C)P(N(C)C)(N(C)C)=O>[C:14]1([C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:1])[C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=2)=[O:20])[S:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 4.27 parts of lithium diisopropylamide and 50 parts of tetrahydrofuran is cooled to -78° C. Then there are added 10.4 parts of methyl 2-[p-(2-thenoyl)phenyl]acetate and the mixture is stirred for 40 minutes. 6.25 Parts of methyl iodide dissolved in 2.15 parts of hexamethylphosphoramide are added at -78° C and the mixture is further stirred for 1 hour after which it is allowed to warm up to room temperature. The whole is poured onto water. The resulting mixture is extracted with diisopropylether. The organic phase is washed with water, dried and evaporated. The residue is crystallized from diisopropylether at 0° C, yielding methyl p-(2-thenoyl)hydratropate.

Workup

additionare added at -78° C
stirringthe mixture is further stirred for 1 hour after which it
temperatureto warm up to room temperature
additionThe whole is poured onto water
extractionThe resulting mixture is extracted with diisopropylether
washThe organic phase is washed with water
customdried
customevaporated
customThe residue is crystallized from diisopropylether at 0° C

Sources & evidence

ORD record: ord-06f904a1e4f14d55b89d8b28f331358d
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04064132

Reaction notes

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