Dimethylformamide → HCID 18650828, compound

HRID 1609426Notes

Reaction equation

HRID 1609426 reaction equation
[H-].[Na+].[CH2:3]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)=[CH:19][N:18]=2)=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:30][C:31]1C=C[C:34](S([O-])(=O)=O)=[CH:33][CH:32]=1.CN(C)C=[O:44]>>[CH2:3]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C@H:33]([CH3:34])[CH2:32][C@@H:31]([OH:44])[CH3:30])=[CH:27][CH:28]=3)=[CH:19][N:18]=2)=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 13907163HCID 13907163, compound

Product 1

HCID 18650828HCID 18650828, compound

Procedure

0.15 g of 55% sodium hydride was mixed with 3 ml of dimethylformamide. A solution of 1.00 g of 4-[2'-(4"-n-octylphenyl)-5-pyrimidinyl]phenol in 2 ml of dimethylformamide was added dropwise thereto under ice-cooling. After the completion of the addition, the obtained mixture was stirred at room temperature for one hour. Then, a solution of 0.79 g of monotosylate of (R,R)-2,4-pentadediol in 2 ml of dimethylformamide was added dropwise thereto and the mixture was stirred at 80° C. for 1.5 hour. After cooling, the reaction mixture was poured into 100 ml of ice-water and extracted with diethyl ether. After washing with water and desolvating, the residue was purified by silica gel column chromatography with the use of a mixture of ethyl acetate and n-hexane (3:7) as a developing solvent to thereby give 0.76 g of the title compound. The obtained product showed the following characteristic absorptions in infrared spectroscopy, which proved that it was the aimed compound.

Workup

  1. temperatureunder ice-cooling
  2. additionAfter the completion of the addition
  3. stirringthe mixture was stirred at 80° C. for 1.5 hour
  4. temperatureAfter cooling
  5. extractionextracted with diethyl ether
  6. washAfter washing with water and desolvating
  7. customthe residue was purified by silica gel column chromatography with the use of a mixture of ethyl acetate and n-hexane (3:7) as a developing solvent

Sources & evidence

ORD record
ord-0d10d1fedef8452fa02c6fb6a6b3fe2e
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

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