Methyl iodide → HCID 22020938, compound

HRID 1793325Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[O:8][C:5]2=[N:6][CH:7]=1.[Li][CH2:22]CCC.IC.[NH4+].[Cl-]>C1COCC1>[CH3:18][C:17]([Si:14]([CH3:16])([CH3:15])[O:13][CH2:12][CH:9]1[O:8][C:5]2=[N:6][CH:7]=[C:2]([CH3:22])[CH:3]=[C:4]2[O:11][CH2:10]1)([CH3:20])[CH3:19]

Participants

Conditions

Temperature: -78 °C

Procedure

Reaction under nitrogen atmosphere. A solution of intermediate (37) (0.00194 mol) in THF was cooled to −78° C. BuLi (0.00214 mol, 2.5M) was added dropwise and the mixture was stirred for 75 minutes at −78° C. Then, iodomethane (00214 mol) was added and the reaction mixture was stirred for 45 minutes. A saturated aqueous NH4Cl solution was added and the mixture was allowed to warm to room temperature. This mixture was extracted with ethyl acetate. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by flash column chromatography over silica gel (eluent: hexane/ethyl acetate 80/20). The desired fractions were collected and the solvent was evaporated, yielding 0.24 g of 3-[[[(1,1-dimethylethyl)dimethyl-silyl]oxy]methyl]-2,3-dihydro-7-methyl-[1,4]dioxino[2,3-b]pyridine (intermediate 38).

Workup

customReaction under nitrogen atmosphere
stirringthe reaction mixture was stirred for 45 minutes
temperatureto warm to room temperature
extractionThis mixture was extracted with ethyl acetate
customThe separated organic layer was dried
filtrationfiltered
customthe solvent evaporated
customThe residue was purified by flash column chromatography over silica gel (eluent: hexane/ethyl acetate 80/20)
customThe desired fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-47a5080b79c24614836794070a39ff48
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081453B2

Reaction notes

Loading…