Tetrahydrofuran → HCID 178469468, compound

HRID 1905705Notes

Reaction equation

HRID 1905705 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][C:9](=[O:12])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18]1COCC1>C[Mg+].[Br-].CCOCC>[OH:1][C:2]1[C:11]2[CH2:10][C:9]([OH:12])([CH3:18])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178469469HCID 178469469, compound

Product 1

HCID 178469468HCID 178469468, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 178418689HCID 178418689, compoundSolvent

Procedure

To a stirred suspension of ethyl 4-hydroxy-6-oxo-5,6,7,8-tetrahydroquinoline 3-carboxylate (12 g) in 250 mL of THF, 35 mL of 3N MeMgBr in Et2O is added dropwise under cooling maintaining the temperature at 0° to 5°. The mixture is stirred for another 1 hour at the same temperature, then quenched and evaporated. The dried residue is taken up in CHCl3, washed with aqueous NaCl, dried (MgSO4) and evaporated to obtain ethyl 4,6-dihydroxy-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate.

Workup

  1. additionis added dropwise
  2. temperatureunder cooling
  3. temperaturemaintaining the temperature at 0° to 5°
  4. customquenched
  5. customevaporated
  6. washwashed with aqueous NaCl
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-87a84b65adbf42788a6972f7172a2dac
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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