Sodium hydride → HCID 19434009, compound

HRID 1735990Notes

Reaction equation

HRID 1735990 reaction equation
[OH:1][CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:20])(=[O:19])[NH:4][CH2:3]1.[H-].[Na+].[CH3:23][O:24][CH2:25][CH2:26]Br>O>[OH:1][CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:16])([CH3:17])[CH3:18])(=[O:12])=[O:13])[S:10][C:6]=2[S:5](=[O:20])(=[O:19])[N:4]([CH2:26][CH2:25][O:24][CH3:23])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 22901902HCID 22901902, compound

Product 1

HCID 19434009HCID 19434009, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Step F (0.3 g, 0.88 mmol) was added to a suspension of sodium hydride (0.05 g of a 60% suspension in mineral oil, rinsed once with hexane, 1.25 mmol) in DMF (5 mL) at 0° C. The cooling bath was removed and the mixture was stirred for one hour at which point 2-bromoethyl methyl ether (0.09 mL, 0.97 mmol) was added. The mixture was stirred for 18 hr at room temperature, water was added and the mixture extracted with ethyl acetate (3×3 mL). The combined extracts were washed with water (10 mL), dried (MgSO4) and evaporated to provide an oil which was purified by column chromatography (silica, hexane/ethyl acetate gradient) to give the desired product as an oil (0.35 g, 100%) which was used in the next reaction.

Workup

  1. washrinsed once with hexane, 1.25 mmol) in DMF (5 mL) at 0° C
  2. customThe cooling bath was removed
  3. additionwas added
  4. extractionthe mixture extracted with ethyl acetate (3×3 mL)
  5. washThe combined extracts were washed with water (10 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto provide an oil which
  9. customwas purified by column chromatography (silica, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-87339aeffe2749ceb595733f8e901a2a
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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