Water → HCID 20399855, compound

HRID 1981135Notes

Reaction equation

HRID 1981135 reaction equation
O=O.[K+].Br[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10].C1OCCOCCOCCOCCOCC[O:23]C1.O>CS(C)=O>[OH:23][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 2855718-Crown-6HCID 6154112030-88-5HCID 20399856HCID 20399856, compound

Product 1

HCID 20399855HCID 20399855, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium superoxide (0.50 g) was added to a solution of 1-(5-bromopentanoyl)-1,2,3,4-tetrahydroquinoline (1.8 g) and 18-Crown-6 (0.4 g) in dimethylsulfoxide (25 ml). After 8 hours the solution was added to water and extracted with ether. The extract was washed, dried and evaporated and the residue was chromatographed on silica gel, eluting with 95:5 methylene chloride:methanol, to yield 1-(5-hydroxypentanoyl)-1,2,3,4-tetrahydroquinoline.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed
  3. customdried
  4. customevaporated
  5. customthe residue was chromatographed on silica gel
  6. washeluting with 95:5 methylene chloride

Sources & evidence

ORD record
ord-6e5f47ae756a4d31bd84564b9c58f193
Source dataset
uspto-grants-1985_04
Patent number
US04512990

Reaction notes

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