Iodide Ion → HCID 18793505, compound

HRID 1004762Notes

Reaction equation

[Li].[CH3:2]C(NC(C)C)C.[F:9][CH:10]([F:27])[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][C:13]=1[O:21][CH:22]1[CH2:26][CH2:25][O:24][CH2:23]1.[I-]>C1COCC1>[F:27][CH:10]([F:9])[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:2])[C:19]#[N:20])=[CH:14][C:13]=1[O:21][CH:22]1[CH2:26][CH2:25][O:24][CH2:23]1

Participants

Conditions

Temperature: -78 °C

Procedure

N-(1-methylethyl)-2-propanamine lithium salt (0.0325 mol; 1 M in THF) was added dropwise and under N2 flow to intermediate 4 (0.0309 mol) in THF (70 ml), cooled to -78° C. The mixture was stirred for 30 minutes at -78° C. lodomethane iodide (0.034 mol) was added dropwise and the reaction mixture was stirred for 2 hours at RT. The mixture was quenched with a saturated aqueous NH4Cl solution, and extracted with ethylacetate. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2), then by HPLC over silica gel (eluent: hexane/ethylacetate 3/2). The pure fractions were collected and the solvent, yielding 4.64 g (53%) of (±)-4-(difluoromethoxy)-alpha-methyl-3-[(tetrahydro-3-furanyl)oxy]benzeneacetonitrile (intermediate 9).

Workup

additionwas added dropwise
customThe mixture was quenched with a saturated aqueous NH4Cl solution
extractionextracted with ethylacetate
customThe separated organic layer was dried
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2)
customThe pure fractions were collected

Sources & evidence

ORD record: ord-f822d8e48bd240d1893071f0ad7f9de1
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051718

Reaction notes

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