Methyl iodide → HCID 23372386, compound

HRID 1898757Notes

Reaction equation

HRID 1898757 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[CH:23]=[C:22]([OH:24])[C:21]([I:25])=[CH:20][C:13]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].IC.[CH3:28]N1CCCN(C)C1=O>C1COCC1>[Si:3]([O:10][CH2:11][C:12]1[CH:23]=[C:22]([O:24][CH3:28])[C:21]([I:25])=[CH:20][C:13]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 23372345HCID 23372345, compound

Product 1

HCID 23372386HCID 23372386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 60% sodium hydride in mineral (1.2 g) in THF (56 ml) is cooled to -20° C. and of solution of methyl 2-tert-butyldimethylsilyloxymethyl-4-hydroxy-5-iodohydrocinnamate (12.6 g), iodomethane (5 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (8 ml) in THF (20 ml) is added. The cold bath is removed, the mixture stirred for about 2 hours, and diluted with ether. The ether solution is washed with 0.1M HCl, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography, eluting with 10% ether in hexanes, to give the desired product.

Workup

  1. additionis added
  2. customThe cold bath is removed
  3. additiondiluted with ether
  4. washThe ether solution is washed with 0.1M HCl, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography
  9. washeluting with 10% ether in hexanes

Sources & evidence

ORD record
ord-0e15711f392e46a188f8fa364e2d5e5c
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

Loading…