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

HRID 452861

Reaction equation

HRID 452861 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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, and 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 oil.

Workup

  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)

Sources & evidence

ORD record
ord-d226a86c646a4f2c83cd6e94dc8b76d3
Source dataset
uspto-grants-2013_07
Patent number
US08492397B2

Linked notes

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