4-Nitrobenzoyl chloride → HCID 59774863, compound

HRID 2422501Notes

Reaction equation

HRID 2422501 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([OH:19])([CH2:16][CH:17]=[CH2:18])[C:4]#[C:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[H-].[Na+].[N+:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O-:26])=[O:25]>CN(C=O)C.O>[N+:24]([C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:19][C:3]([C:2]([F:1])([F:20])[F:21])([C:4]#[C:5][Si:6]([CH:13]([CH3:14])[CH3:15])([CH:10]([CH3:11])[CH3:12])[CH:7]([CH3:8])[CH3:9])[CH2:16][CH:17]=[CH2:18])=[O:32])=[CH:34][CH:35]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 24758Sodium hydrideHCID 59774920HCID 59774920, compound

Product 1

HCID 59774863HCID 59774863, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a 0° C. solution of crude 3-(trifluoromethyl)-1-(triisopropylsilyl)hex-5-en-1-yn-3-ol from Step 1 (242 mg, 0.755 mmol) in DMF (2 mL) was added NaH (60% disp., 32 mg, 0.793 mmol) in two portions. The mixture was allowed to reach room temperature and stirred for 40 min. A solution of 4-nitrobenzoyl chloride (147 mg, 0.793 mmol) in DMF (1 mL) was added dropwise. After 1.5 h, the mixture was poured in H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O (3×) and brine, dried (Na2SO4) and concentrated, affording the title compound (342 mg).

Workup

  1. customto reach room temperature
  2. waitAfter 1.5 h
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with H2O (3×) and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2060469509be43139097706ff72b8386
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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