4-Nitrobenzoyl chloride → 3-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoate
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([OH:12])([CH2:10][CH3:11])[C:4]#[C:5][Si](C)(C)C.[H-].[Na+].[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18]>CN(C=O)C>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:12][C:3]([CH2:10][CH3:11])([C:2]([F:14])([F:13])[F:1])[C:4]#[CH:5])=[O:25])=[CH:27][CH:28]=1)([O-:19])=[O:18]Participants
Procedure
To a stirred solution of 3-(trifluoromethyl)-1-(trimethylsilyl)pent-1-yn-3-ol (10.5 g, 46.9 mmol) in DMF (140 mL), sodium hydride (60% in oil, 1.9 g, 46.9 mmol) was added portionwise. After 25 min stirring, a solution of 4-nitrobenzoyl chloride (8.7 g, 46.9 mmol) in 50 mL DMF was added slowly. The reaction mixture was then stirred at room temperature for 2 hours. The reaction mixture was quenched with pH 7 buffer 25% NH4OAc aq solution (500 mL) and the product was extracted with diethyl ether (4×), washed with water (3×) and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (Ethyl acetate/hexanes, 15:85). 1H NMR (400 MHz, acetone-d6): 8.45 (d, 2H), 8.27 (d, 2H), 3.69 (s, 1H), 2.60-2.40 (m, 2H), 1.16 (t, 3H).
Workup
- stirringThe reaction mixture was then stirred at room temperature for 2 hours
- customThe reaction mixture was quenched with pH 7 buffer 25% NH4OAc aq solution (500 mL)
- extractionthe product was extracted with diethyl ether (4×)
- washwashed with water (3×) and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2e9c3d9c42e4464283aadf13974502ac
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960409B2
Reaction notes
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