Benzyl chloroformate → HCID 178469471, compound

HRID 649596Notes

Reaction equation

HRID 649596 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-dihydroxy-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-51e14cdf7b6b4eb4be05b59d5749a6d4
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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