Sodium hydride → HCID 19744891, compound

HRID 2254235Notes

Reaction equation

HRID 2254235 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[C:17](=[O:34])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH2:29][O:30][CH3:31])=[C:22]([O:32][CH3:33])[CH:21]=1.[H-].[Na+].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>CN(C)C=O>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([O:15][CH3:16])[C:3]([C:17](=[O:34])[CH2:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH2:29][O:30][CH3:31])=[C:22]([O:32][CH3:33])[CH:21]=2)=[C:2]([O:1][CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:7]=1[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 14368075HCID 14368075, compound

Product 1

HCID 19744891HCID 19744891, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 10 ml of dimethylformamide was dropped into a mixture of 2.3 g of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1-propanone and 0.2 g of sodium hydride at 0° C., and the mixture was stirred for 45 minutes. Then, 0.5 ml of methyl α-bromoacetate was added to the mixture at 0° C., and the mixture was stirred for 20 minutes. After the reaction, the solvent was removed from the reaction liquid mixture by distillation and the residue was dried under a reduced pressure to obtain substantially quantitatively 1-(4,6-dimethoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1-propanone in the form of a colorless transparent oil.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. customAfter the reaction
  3. customthe solvent was removed from the reaction liquid mixture by distillation
  4. customthe residue was dried under a reduced pressure

Sources & evidence

ORD record
ord-603b2c2a6b6c40e8b86424f94da40660
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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