Dimethylformamide → HCID 11402394, compound

HRID 2250305Notes

Reaction equation

HRID 2250305 reaction equation
Br[CH2:2][CH:3]1[O:7][C:6]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)([CH3:8])[O:5][C:4]1=[O:19].CN(C)C=O>C(OC(C)C)(C)C>[CH2:2]=[C:3]1[O:7][C:6]([C:9]23[CH2:16][CH:15]4[CH2:17][CH:11]([CH2:12][CH:13]([CH2:14]4)[CH2:18]2)[CH2:10]3)([CH3:8])[O:5][C:4]1=[O:19]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 23022609HCID 23022609, compound

Product 1

HCID 11402394HCID 11402394, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture obtained by dissolving 16.4 g (0.05 mol) of 5-bromomethyl-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one in 58 g of isopropyl ether was placed in a flask equipped with an agitator, a thermometer, a condenser and a dropping funnel. 36.5 g (0.5 mol) of N,N-dimethylformamide was added by drops thereto, followed by intensively stirring at room temperature for 4 hours. After completion of the stirring, insoluble products were removed from the reaction solution by filtration, and the obtained filtrate was transferred into a 500 ml separatory funnel. The solution was left at rest, so as to separate it into two layers, and the lower N,N-dimethylformamide layer was removed. The upper isopropyl ether layer washed with water to remove N,N-dimethylformamide dissolved therein. Thereafter, isopropyl ether was removed, so as to obtain white crystals. The obtained white crystals were recrystallized from hexane, so as to obtain 6.6 g of 5-methylene-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one (hereinafter referred to as AdMDO) (yield: 53%).

Workup

  1. customA mixture obtained
  2. customwas placed in a flask
  3. customequipped with an agitator
  4. customAfter completion of the stirring, insoluble products were removed from the reaction solution by filtration
  5. customthe obtained filtrate was transferred into a 500 ml separatory funnel
  6. waitThe solution was left at rest
  7. customso as to separate it into two layers
  8. customthe lower N,N-dimethylformamide layer was removed
  9. washThe upper isopropyl ether layer washed with water
  10. customto remove N,N-dimethylformamide
  11. dissolutiondissolved
  12. customThereafter, isopropyl ether was removed
  13. customso as to obtain white crystals
  14. customThe obtained white crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-0abcbf8cbe0641b3a851ecd5ce193e2d
Source dataset
uspto-grants-2008_01
Patent number
US07316884B2

Reaction notes

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