Dimethylformamide → HCID 54511176, compound

HRID 412853Notes

Reaction equation

HRID 412853 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:14][C@H:15]1[C@@H:28]([OH:29])[C@@H:27]([CH2:30][O:31][CH2:32][CH:33]=[CH2:34])[O:26][C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]1O)[CH:12]=[CH2:13].CN(C)[CH:38]=[O:39]>CO>[CH2:11]([O:14][C@H:15]1[C@@H:28]([O:29][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:27]([CH2:30][O:31][CH2:32][CH:33]=[CH2:34])[O:26][C@@H:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@@H:16]1[O:39][CH2:38][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 54063239HCID 54063239, compound

Product 1

HCID 54511176HCID 54511176, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under nitrogen gas atmosphere and ice cooling, benzyl bromide (11.4 ml, 95.5 mmol) was added to a mixture of 60% sodium hydride (3.8 g, 95.5 mmol), Compound 11 (6.7 g, 19.1 mmol) and dimethylformamide (20 ml), and the mixture was stirred for 18 hours. Methanol was added to the reaction mixture under ice cooling and stirred for 1 hour, and the solvent was evaporated under reduced pressure. The residue was diluted with diethyl ether, washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1-9:1) to obtain Compound 12 (9.1 g, 90%).

Workup

  1. stirringstirred for 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with diethyl ether
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1-9:1)

Sources & evidence

ORD record
ord-28c75ac2d2e449929cfa83cdb3050f63
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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