Methanol → HCID 9861674, compound

HRID 485161Notes

Reaction equation

HRID 485161 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[C:4]=2[CH:3]=C1.C[OH:23]>>[CH:3]([C:4]1[C:5]([OH:1])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])=[O:23]

Participants

3

Reactant 2

HCID 887MethanolHCID 13092112HCID 13092112, compound

Product 1

HCID 9861674HCID 9861674, compound

Conditions

Temperature
-65 °C

Procedure

5-(4-Benzofuranyloxy)-N-methylsulphonylpentanamide (0.933 g, 0.003 M) was dissolved in dry methanol (135 ml) and cooled to -65° C. with stirring and exclusion of moisture. Ozonised air was bubbled through the solution at a rate of 20 liters/hr for 45 mins. Nitrogen was then bubbled through the solution (5 mins) to remove excess ozone before the addition of dimethyl sulphide (0.9 ml). The mixture was allowed to warm to room temperature overnight (16 hr). The solvent was removed in vacuo, the residue dissolved in ethyl acetate-ether (1:1), washed with water and extracted with 5% sodium bicarbonate solution. The combined extracts were acidified with concentrated hydrochloric acid the precipitated solid was filtered off, washed wall with water and recrystallised from ethyl acetate-petrol to give 5-(2-formyl-3-hydroxyphenoxy)-N-methylsulphonylpentanamide, m.p. 136°-138° C. (Found: C, 49.54; H, 5.33; N. 4.12, S, 10.14. C13H17NSO6 requires C, 49.51; H, 5.43; N, 4.44; S, 10.17%).

Workup

  1. customwas bubbled through the solution at a rate of 20 liters/hr for 45 mins
  2. customNitrogen was then bubbled through the solution (5 mins)
  3. customto remove excess ozone
  4. additionbefore the addition of dimethyl sulphide (0.9 ml)
  5. temperatureto warm to room temperature overnight (16 hr)
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue dissolved in ethyl acetate-ether (1:1)
  8. washwashed with water
  9. extractionextracted with 5% sodium bicarbonate solution
  10. filtrationwas filtered off
  11. washwashed wall with water
  12. customrecrystallised from ethyl acetate-petrol

Sources & evidence

ORD record
ord-8ab7620d4f554c349fa95d3687b20547
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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