Hydrochloric Acid → HCID 68756210, compound

HRID 452856Notes

Reaction equation

HRID 452856 reaction equation
[F:1][C:2]([F:7])([F:6])[C@@H:3]([OH:5])[CH3:4].Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10].CN(C)CCO.Cl>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:9](=[O:10])([O:5][C@@H:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])[O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanolHCID 821294-Nitrophenyl chloroformateHCID 6999971(2S)-1,1,1-Trifluoropropan-2-ol

Product 1

HCID 68756210HCID 68756210, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-(−)-1,1,1-trifluoro-2-propanol (1.95 g) in CHCl3 (30 ml) was added 4-nitrophenyl chloroformate (5.16 g) and pyridine (135 g) at room temperature. After 1-hour stirring at 60° C., the resulting mixture was cooled to room temperature. To the resulting mixture was added 2-(dimethylamino)ethanol (1.52 g) and was stirred at room temperature for 1 hour. The mixture was poured into 1 M aqueous solution of HCl and extracted with CHCl3. The extract was washed with water and then dried over Na2SO4 and concentrated. The residue was purified with silica gel column chromatography (eluent:hexane/EtOAc=1/0˜50/50) to give 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate as a pale yellow oil.

Workup

  1. temperaturethe resulting mixture was cooled to room temperature
  2. stirringwas stirred at room temperature for 1 hour
  3. extractionextracted with CHCl3
  4. washThe extract was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (eluent:hexane/EtOAc=1/0˜50/50)

Sources & evidence

ORD record
ord-0cd535aac58d4f22873791f248e26e64
Source dataset
uspto-grants-2013_07
Patent number
US08492397B2

Reaction notes

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