Sodium hydride → HCID 19744891, compound

HRID 1030719Notes

Reaction equation

HRID 1030719 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-d2ec9dd653ea4bfaa93c9b57948d8070
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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