1,1,1-Trifluoro-2-methylpropan-2-ol → 4-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

HRID 2383510

Reaktionsgleichung

Reaktionsgleichung von HRID 2383510
[F:1][C:2]([F:8])([F:7])[C:3]([CH3:6])([OH:5])[CH3:4].C([Li])CCC.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:15](=[O:16])([O:5][C:3]([CH3:6])([CH3:4])[C:2]([F:8])([F:7])[F:1])[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

7

Edukt 3

HCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 821294-Nitrophenyl chloroformateHCID 178418339Butyllithium

Produkt 1

HCID 577851834-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1,1,1-trifluoro-2-methylpropan-2-ol (1.0 g) in THF (30 mL) was added a 2M solution of n-butyl lithium in n-hexane (3.9 mL) and then 4-nitrophenyl chloroformate (2.4 g) at −75° C. The mixture was warmed to room temperature and diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% EtOAc/Hexane) to give 4-nitrophenyl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate as a pale yellow foam.

Aufarbeitung

  1. customat −75° C
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3bf51f7a5c41482e8f8af026c33c8c4c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263632B2

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