Sodium hydride → HCID 19744901, compound

HRID 1030715Notes

Reaction equation

HRID 1030715 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:32])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][O:30][CH3:31])[CH:21]=1.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38]>CN(C)C=O>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([O:15][CH3:16])[C:3]([C:17](=[O:32])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][O:30][CH3:31])[CH:21]=2)=[C:2]([O:1][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:7]=1[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 14368072HCID 14368072, compound

Product 1

HCID 19744901HCID 19744901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 20 ml of dimethylformamide was dropped into a mixture of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(4-methoxy-3-methoxymethoxyphenyl)-1-propanone and 0.4 g of sodium hydride at 0° C., and the mixture was stirred for 30 minutes. Then, 1.0 ml of methyl α-bromoacetate was added to the mixture at 0° C. and the mixture was stirred for 30 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-(4-methoxy-3-methoxymethoxyphenyl)-1-propanone in the form of a colorless transparent oil.

Workup

  1. stirringthe mixture was stirred for 30 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-bda36f1b5c2a4c9a83f4be20af46ad63
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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