Dimethylformamide → HCID 19068293, compound

HRID 1957698Notes

Reaction equation

HRID 1957698 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[OH:27])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CN(C=O)C.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38]>O>[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 19068288HCID 19068288, compound

Product 1

HCID 19068293HCID 19068293, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.1 g (5.79 mmol) of benzyl 3-(1-adamantyl)-4-hydroxybenzoate and 20 ml of DMF were introduced into a three-necked flask and 191 mg (6.34 mmol) of sodium hydride (80% in oil) were added portionwise. The mixture was stirred until the evolution of gas had ceased, then 565 μl (5.79 mmol) of methyl bromoacetate were added and the mixture was stirred at room temperature for twelve hours. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The solid was triturated from hexane, filtered off and dried. 2.36 g (94%) of the expected compound, having a melting point of 134°-5° C., were recovered.

Workup

  1. stirringthe mixture was stirred at room temperature for twelve hours
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe solid was triturated from hexane
  7. filtrationfiltered off
  8. customdried
  9. customwere recovered

Sources & evidence

ORD record
ord-67690ddab99c4b2c9848634b3721af3d
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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