Water → HCID 12888747, compound

HRID 1278023Notes

Reaction equation

HRID 1278023 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]1[O:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7]1)[CH:2]=[CH2:3].Cl[CH2:14][C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16].[H-].[Na+].O>CS(C)=O>[CH2:18]([N:17]([CH2:21][CH2:22][CH3:23])[C:15](=[O:16])[CH2:14][O:12][CH2:11][CH:9]1[CH2:8][CH2:7][CH:6]([CH2:5][O:4][CH2:1][CH:2]=[CH2:3])[O:10]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2196472-chloro-N,N-dipropylacetamideHCID 12888746Tetrahydro-5-[(2-propenyloxy)methyl]-2-furanmethanol

Product 1

HCID 12888747HCID 12888747, compoundYield 141%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 6.89 g of tetrahydro-5-[(2-propenyloxy)methyl]-2-furanmethanol (0.04 mole) and 7.12 g of 2-chloro-N,N-dipropylacetamide (0.02 mole) are dissolved in 200 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 removed in vacuo yielding a pale yellow oil which is vacuum distilled and the fraction distilling at 185°-188° @ 0.5 mm is collected yielding 8.84 g (70%) 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 CHCl3 layer is separated
  14. dry with materialdried over anhydrous Na2SO4 overnight
  15. customThe CHCl3 is removed in vacuo
  16. customyielding a pale yellow oil which
  17. distillationdistilled
  18. distillationthe fraction distilling at 185°-188° @ 0.5 mm
  19. customis collected

Sources & evidence

ORD record
ord-06d1c24a64024e74b29098c092bf4f46
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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