4-Nitrobenzoyl chloride → HCID 59774865, compound

HRID 2422496Notes

Reaction equation

HRID 2422496 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([CH3:11])([OH:10])[C:4]#[C:5][Si](C)(C)C.[H-].[Na+].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>CN(C=O)C>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:10][C:3]([CH3:11])([C:2]([F:13])([F:12])[F:1])[C:4]#[CH:5])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 24758Sodium hydrideHCID 59774880HCID 59774880, compound

Product 1

HCID 59774865HCID 59774865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of crude 1,1,1-trifluoro-2-methyl-4-(trimethylsilyl)but-3-yn-2-ol from Step 1 (˜20.2 mmol) in DMF (10 mL) was added dropwise to a suspension of NaH (60% disp., 850 mg, 21.2 mmol) in DMF (25 mL) at 0° C. The mixture was allowed to reach room temperature, stirred for 30 min. and recooled to 0° C. A solution of 4-nitrobenzoyl chloride (3.94 g, 21.2 mmol) in DMF (10 mL) was added dropwise and the resulting mixture was stirred at room temperature. After 30 min., the mixture was poured in 1:1 25% NH4OAc/H2O and extracted with Et2O (3×). The combined organic layers were washed with H2O (3×) and brine, dried (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (toluene/hexane 40:60 to 60:40) affording the title compound. 1H NMR (400 MHz, acetone-d6): 8.44 (d, 2H), 8.28 (d, 2H), 3.65 (s, 1H), 2.09 (s, 3H).

Workup

  1. customto reach room temperature
  2. customrecooled to 0° C
  3. stirringthe resulting mixture was stirred at room temperature
  4. waitAfter 30 min.
  5. extractionextracted with Et2O (3×)
  6. washThe combined organic layers were washed with H2O (3×) and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aeea033657b9437798067a2dca8f2048
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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