Water → 2-[[5-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanyl]-methoxy]-N,N-dipropylacetamide

HRID 1278026Notes

Reaction equation

HRID 1278026 reaction equation
[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([CH2:7][O:8][CH2:9][CH:10]2[O:14][CH:13]([CH2:15][OH:16])[CH2:12][CH2:11]2)[CH2:4][O:3]1.Cl[CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21].[H-].[Na+].O>CS(C)=O>[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([CH2:7][O:8][CH2:9][CH:10]2[O:14][CH:13]([CH2:15][O:16][CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21])[CH2:12][CH2:11]2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2196472-chloro-N,N-dipropylacetamideHCID 128887485-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanmethanol

Product 1

HCID 128887492-[[5-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanyl]-methoxy]-N,N-dipropylacetamideYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4.93 g of 5-[[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]methyl]tetrahydro-2-furan-methanol (0.02 mole) and 3.55 g of 2-chloro-N,N-dipropylacetamide (0.02 mole) are dissolved in 125 ml of dry dimethyl sulfoxide and the mixture stirred at room temperature under nitrogen. Slowly 0.50 g of sodium hydride (0.02 mole) is added to the dimethyl sulfoxide mixture and the reaction allowed to stir at ambient temperature (23°). After stirring for 10 minutes an exothermic reaction begins to take place and an ice-bath is used to maintain the reaction temperature below 30°. After stirring for 1 hour the ice-bath is removed and the reaction allowed to stir at room temperature for 18 hours. The excess NaH is destroyed by adding 5 ml of methanol and the entire reaction mixture is then poured into 400 ml of water. The product is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined and washed with 4× 300 ml portions of water. The CHCl3 layer is separated and dried over anhydrous Na2SO4 overnight. The CHCl3 is then removed in vacuo yielding a pale yellow oil which is vacuum distilled through a 10 cm vigreux column and the fraction distilling at 91°-94° @ 0.4 mm is collected, yielding 4.86 g (63%) of the above compound.

Workup

  1. stirringto stir at ambient temperature (23°)
  2. stirringAfter stirring for 10 minutes
  3. customan exothermic reaction
  4. temperatureto maintain the reaction temperature below 30°
  5. customis removed
  6. stirringto stir at room temperature for 18 hours
  7. customThe excess NaH is destroyed
  8. additionby adding 5 ml of methanol
  9. customthe entire reaction mixture
  10. extractionThe product is extracted with 3×125 ml portions of chloroform
  11. washwashed with 4× 300 ml portions of water
  12. customThe CHCl3 layer is separated
  13. dry with materialdried over anhydrous Na2SO4 overnight
  14. customThe CHCl3 is then removed in vacuo
  15. customyielding a pale yellow oil which
  16. distillationdistilled through a 10 cm vigreux column
  17. distillationthe fraction distilling at 91°-94° @ 0.4 mm
  18. customis collected

Sources & evidence

ORD record
ord-86c5d02805a0467a9ef97e16038ebafe
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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