Sodium hydride → HCID 19744894, compound

HRID 2254227Notes

Reaction equation

HRID 2254227 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][CH2:27][O:28][CH3:29])=[C:22]([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][CH2:27][O:28][CH3:29])=[C:22]([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 14368069HCID 14368069, compound

Product 1

HCID 19744894HCID 19744894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 10 ml of dimethylformamide was dropped into a mixture of 2.0 g of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(3-methoxy-4-methoxymethoxyphenyl)-1-propanone and 0.2 g of sodium hydride, and the mixture was stirred for 60 minutes. Then, 0.5 ml of methyl α-bromoacetate was added to the mixture at 0° C., and the mixture was stirred for 45 minutes. After the reaction, the solvent was removed from the reaction liquid mixture by distillation, and the residue was dried under reduced pressure to obtain substantially quantitatively 1-(4,6-dimethoxy- 2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(3-methoxy-4-methoxymethoxyphenyl)-1-propanone in the form of a colorless transparent oil.

Workup

  1. stirringthe mixture was stirred for 45 minutes
  2. customAfter the reaction
  3. customthe solvent was removed from the reaction liquid mixture by distillation
  4. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-1c0bf8f2b75e4af1ac74b4800a09c306
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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