Methyl iodide → 2-tert-Butyldimethylsilyloxymethyl-6-(1-methoxy-1-methylethyl)pyridine

HRID 876996Notes

Reaction equation

HRID 876996 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:21])([CH3:20])[CH3:19])[N:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:22]I>CN(C=O)C>[Si:3]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:21][CH3:22])([CH3:20])[CH3:19])[N:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66718395HCID 66718395, compound

Product 1

HCID 667184232-tert-Butyldimethylsilyloxymethyl-6-(1-methoxy-1-methylethyl)pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

NaH (285 mg, 7.12 mmol) was added portionwise to a stirred solution of 2-tert-butyldimethylsilyloxymethyl-6-(1-hydroxy-1-methylethyl)pyridine (2.0 g, 7.12 mmol) in DMF (30 mL) at room temperature. After 20 min, methyl iodide (1.33 mL, 21.4 mmol) was added, the mixture was warmed to 50° C. and stirred for 16 h at this temperature. The mixture was poured onto water, extracted with EtOAc (×3), the combined extracts were dried (MgSO4), filtered evaporated and the residue purified by column chromatography (20:1 to 10:1, isohexane:EtOAc) to give the title compound (1.20 g, 57%) as a colorless oil; NMR δH (400 MHz, CDCl3) 7.69-7.65 (1H, m), 7.38-7.34 (2H, m), 4.81 (2H, s), 3.15 (3H, s), 1.53 (6H, s), 0.96 (9H, s), 0.12 (6H, s).

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with EtOAc (×3)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue purified by column chromatography (20:1 to 10:1, isohexane:EtOAc)

Sources & evidence

ORD record
ord-c4f26afc329c44ffa1e6ddb42a481063
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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