Benzyl chloroformate → HCID 178469471, compound

HRID 1194552Notes

Reaction equation

HRID 1194552 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH:9]([OH: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].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)(Cl)Cl>[CH2:22]([O:21][C:19]([O:12][CH:9]1[CH2:8][CH2:7][C:6]2[N:5]=[CH:4][C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:2]([OH:1])[C:11]=2[CH2:10]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 178469470HCID 178469470, compound

Product 1

HCID 178469471HCID 178469471, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A well stirred mixture of 5 g of ethyl 4,6-di-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylate and 3.0 g of KHCO3 in 300 mL of CHCl3 is ice-cooled. To the cooled mixture, benzyl chloroformate (3.6 g) is added over a period of 10 minutes maintaining the reaction temperature below 10°. The reaction mixture is vigorously stirred at room temperature overnight, then filtered. The filtrate is washed with H2O, dried (MgSO4), and evaporated to dryness. The dried residue is purified by flash chromatography on a silica gel column to yield ethyl 6-benzyloxycarbonyloxy-4-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylate

Workup

  1. temperaturecooled
  2. temperaturemaintaining the reaction temperature below 10°
  3. stirringThe reaction mixture is vigorously stirred at room temperature overnight
  4. filtrationfiltered
  5. washThe filtrate is washed with H2O
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe dried residue is purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-19b78a95ad874616b8492d5184192c3e
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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