1,4-Dioxane--water (1/1) → HCID 178504544, compound

HRID 617915Notes

Reaction equation

HRID 617915 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@:20]([O:30][SiH:31]([CH3:33])[CH3:32])([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]=O)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[O:34]1[CH2:39][CH2:38][O:37]CC1.O>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@:20]([O:30][SiH:31]([CH3:32])[CH3:33])([C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22][C:23]4[CH:24]=[CH:4][CH:3]=[CH:2][C:11]=4[C:39]([CH:38]=[O:37])=[O:34])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 178504554HCID 178504554, compound

Product 1

HCID 178504544HCID 178504544, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To predissolved SeO2 (2.95 g, 26.57 mmol) in dioxane/H2O mixture (100 mL:0.48 mL) at 60∞C, was added the ketone from Step 1 (14.4 g, 26 mmol) in solution in dioxane (70 mL). The reaction mixture was heated at 100∞C overnight. The reaction was cooled to room temperature and filtered through a pad of celite and washed with dioxane (20 mL). Evaporation to dryness yielded the title compound which was used as such in the next step (Crude weight 14 g).

Workup

  1. temperatureThe reaction mixture was heated at 100∞C overnight
  2. filtrationfiltered through a pad of celite
  3. washwashed with dioxane (20 mL)
  4. customEvaporation to dryness

Sources & evidence

ORD record
ord-a48f6fce58d3490e96bfadb7812fcf43
Source dataset
uspto-grants-1999_09
Patent number
US05952347

Reaction notes

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