Benzyl Alcohol → HCID 19417346, compound

HRID 864894Notes

Reaction equation

HRID 864894 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:23])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:11]([O:19][CH2:20][CH3:21])[C:10]=2[CH3:22])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)C1C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[H-].[Na+]>C1COCC1>[CH2:40]([O:47][C:2]1[C:7]([C:8](=[O:23])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:11]([O:19][CH2:20][CH3:21])[C:10]=2[CH3:22])=[C:6]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:5]=[CH:4][N:3]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 7657Dibenzyl etherHCID 24758Sodium hydrideHCID 19417345HCID 19417345, compound

Product 1

HCID 19417346HCID 19417346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of step (b) (0.49 g, 1.26 mmol) in 5 ml THF at -20° C. under nitrogen was added a slurry of benzyl oxide (73.78 mmol) generated from benzyl alcohol and oil free sodium hydride in 2 ml THF. The reaction mixture was allowed to warm to room temperature and stirred for several hours, then partitioned between ether and water. The organic layers were dried and evaporated to yield 0.5 g of a crude product. This was purified via chromatography on silica gel using 25% ethyl acetate in hexanes as the eluant to give 0.177 g of 2,4-dibenzyloxy-3-(3-ethoxy-2-methyl-4-methylsulfonylbenzoyl)pyridine, a viscous yellow oil.

Workup

  1. custompartitioned between ether and water
  2. customThe organic layers were dried
  3. customevaporated
  4. customto yield 0.5 g of a crude product
  5. customThis was purified via chromatography on silica gel using 25% ethyl acetate in hexanes as the eluant

Sources & evidence

ORD record
ord-70e59825b90449f393151efa1d74c91d
Source dataset
uspto-grants-1996_10
Patent number
US05565413

Reaction notes

Loading…