Phosgene → 9(+)-Fluorenylethyl chloroformate

HRID 440342Notes

Reaction equation

HRID 440342 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][OH:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17](Cl)([Cl:19])=[O:18]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:19][C:17]([O:16][CH2:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:18]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 10921761Fluorene-9-ethanol

Product 1

HCID 149683719(+)-Fluorenylethyl chloroformate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-(9-Fluorenyl)ethyl chloroformate was prepared from a solution of 2-(9-fluorenyl)ethanol (1.26 g, 6.0 mmol) in 10 ml of toluene and 4 ml of tetrahydrofuran, which was added to 12 ml of phosgene solution (12.4 mol, [1.93M in toluene). The solution was stirred for 1 hour and put under vacuum to remove the phosgene. Concentration yielded 2-(9-fluorenyl)ethyl chloroformate (1.64 g, 6.0 mmol).

Workup

  1. customto remove the phosgene
  2. concentrationConcentration

Sources & evidence

ORD record
ord-62a8f24cbf3a44f19646be1fcb080ece
Source dataset
uspto-grants-1996_05
Patent number
US05519043

Reaction notes

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