Water → N,N-Dipropyl-2-[[tetrahydro-5-[(phenylmethoxy)methyl]-2-furanyl]methoxy]acetamide

HRID 1278016Notes

Reaction equation

HRID 1278016 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH:10]2[O:14][CH:13]([CH2:15][OH:16])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:18][C:19]([N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[O:20].[H-].[Na+].O>CS(C)=O>[CH2:22]([N:21]([CH2:25][CH2:26][CH3:27])[C:19](=[O:20])[CH2:18][O:16][CH2:15][CH:13]1[CH2:12][CH2:11][CH:10]([CH2:9][O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:14]1)[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2196472-chloro-N,N-dipropylacetamideHCID 12888742Tetrahydro-5-[(phenylmethoxy)methyl]-2-furanmethanol

Product 1

HCID 12888743N,N-Dipropyl-2-[[tetrahydro-5-[(phenylmethoxy)methyl]-2-furanyl]methoxy]acetamideYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4.44 g of tetrahydro-5-[(phenylmethoxy)methyl]-2-furanmethanol (0.02 mole) and 3.55 g of 2-chloro-N,N-dipropylacetamide (0.02 mole) is 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 CHCl 3 is then removed in vacuo yielding a pale yellow oil which is vacuum distilled and the fraction distilling at 210°-225° @0.5 mm is collected yielding 5.2 g (72%) 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. stirringAfter stirring for 1 hour
  6. customthe ice-bath is removed
  7. stirringto stir at room temperature for 18 hours
  8. customThe excess NaH is destroyed
  9. additionby adding 5 ml of methanol
  10. customthe entire reaction mixture
  11. extractionThe product is extracted with 3×125 ml portions of chloroform
  12. washwashed with 4×300 ml portions of water
  13. customThe CHCl 3 is then removed in vacuo
  14. customyielding a pale yellow oil which
  15. distillationdistilled
  16. distillationthe fraction distilling at 210°-225° @0.5 mm
  17. customis collected

Sources & evidence

ORD record
ord-341c7289ca014e4994f86726c9428852
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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