1,1,1-Trifluorobutan-2-one → HCID 59774916, compound

HRID 2422494Notes

Reaction equation

HRID 2422494 reaction equation
[F:1][C:2]([C:5]([CH2:7][CH3:8])=[O:6])([F:4])[F:3].[C:9]([Mg]Br)#[C:10][CH3:11]>C1COCC1>[F:1][C:2]([F:4])([F:3])[C:5]([OH:6])([C:9]#[C:10][CH3:11])[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 2382881,1,1-Trifluorobutan-2-oneHCID 178419101HCID 178419101, compound

Product 1

HCID 59774916HCID 59774916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl trifluoromethyl ketone (5.00 g, 40.0 mmol) in THF (20 ml) at room temperature was added 1-propynyl magnesium bromide (0.5 M in THF, 60 mL, 30.0 mmol). The reaction mixture was allowed to stand at rt 1 h, and concentrated in vacuo. The residue was partitioned between Et2O and aq. NH4OAc, the phases were separated, and the organic phase washed with brine, dried over MgSO4, filtered and concentrated (not to complete dryness), to afford a 50 wt. % solution (estimated by 1H NMR) of the title compound (remainder THF and Et2O), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 6.63 (s, 1H), 1.87 (s, 3H), 1.75-1.63 (m, 2H), 1.04 (t, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between Et2O and aq. NH4OAc
  3. customthe phases were separated
  4. washthe organic phase washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated (not to complete dryness),

Sources & evidence

ORD record
ord-3e3017f1d3584f9489f4860cab98269c
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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