tert-Butanol → HCID 22628263, compound

HRID 278580Notes

Reaction equation

HRID 278580 reaction equation
[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].[CH:12](=O)[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].[CH3:21][C:22]([CH3:25])([O-:24])[CH3:23].[K+].[C:27]([OH:31])(C)(C)C>>[O:15]1[C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH:12]=[C:1]([S:3]([N:6]2[CH2:7][CH2:8][N:9]([C:27]([O:24][C:22]([CH3:25])([CH3:23])[CH3:21])=[O:31])[CH2:10][CH2:11]2)(=[O:5])=[O:4])[CH2:2]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 6998SalicylaldehydeHCID 226281081-(Ethenesulfonyl)piperazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22628263HCID 22628263, compound

Procedure

A solution of 1-(ethenesulfonyl)piperazine (1.38 g), salicylaldehyde (610 mg) and potassium tert-butoxide (168 mg) in tert-butanol (20 ml) was refluxed for 4 days. The reaction solution was concentrated, and to the residue was added ethyl acetate. The organic layer was washed with water and brine, dried, concentrated and purified with silica gel column chromatography (hexane/ethyl acetate=2/1) to give a colorless solid of 1-(2H-benzopyrane-3-sulfonyl)-4-(tert-butoxycarbonyl)piperazine (420 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue was added ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified with silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-23e071bc82c84d3ea7a678da1427c7a2
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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