Methyl iodide → HCID 58703560, compound

HRID 1179466Notes

Reaction equation

HRID 1179466 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:9]=1.[CH3:20]I>CN(C=O)C>[Br:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[C:6]([CH2:14][O:15][CH3:20])[C:5]=1[O:16][CH2:17][O:18][CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58703546HCID 58703546, compound

Product 1

HCID 58703560HCID 58703560, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Add sodium hydride (0.430 g of 60% in oil, 10.75 mmol) to DMF (100 mL) at −5° C. Add (3-bromo-2,5-bis-methoxymethoxy-phenyl)-methanol (3.00 g, 9.77 mmol) in DMF (20 mL) in portions and stir the resulting solution at −5° C. for 1 hour. Add methyl iodide (0.67 mL, 10.75 mmol) and stir the reaction for 1 hour. Pour the reaction into ice-H2O (200 mL) and extract with EtOAc (2×50 mL). Combine the extracts and wash with H2O (2×100 mL) and brine (50 mL) then dry (MgSO4), filter and concentrate. Purify the residue by silica gel chromatography eluting with Hex:EtOAc (80:20) to provide the subtitled product (2.76 g, 88%) as an oil. 1H NMR (CDCl3) δ 3.41 (s, 3H), 3.47 (s, 3H), 3.62 (s, 3H), 4.54 (s, 2H), 5.03 (s, 2H), 5.13 (s, 2H), 7.06 (d, J=2.9 Hz, 1H), 7.20 (d, J=2.9 Hz, 1H).

Workup

  1. customthe reaction for 1 hour
  2. additionPour
  3. extractionextract with EtOAc (2×50 mL)
  4. washCombine the extracts and wash with H2O (2×100 mL) and brine (50 mL)
  5. dry with materialthen dry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by silica gel chromatography
  9. washeluting with Hex

Sources & evidence

ORD record
ord-99e612fcac1442d89501ee9a7a65b484
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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