反応 #1121762

反応方程式

NaH

6

4-Bromopyrrole-2-carboxaldehyde

p-toluenesulfonyl chloride

→

crystals

収率 68.6%

4-Bromo-2-formyl-N-p-tosylpyrrole

収率 68.6%

溶媒

THF

反応条件

後処理

1. 1
   workup.WAITAfter 16 h
2. 2
   その他The reaction mixture was quenched
3. 3
   workup.ADDITIONby adding aqueous NH4Cl
4. 4
   workup.ADDITIONEthyl acetate was added
5. 5
   その他the organic layer was separated
6. 6
   洗浄The organic layer was washed with water, brine
7. 7
   乾燥dried (Na2SO4)
8. 8
   濃縮Concentration
9. 9
   その他followed by crystallization (ethyl acetate/hexanes)

実験手順

Following a reported procedure,18 a stirred suspension of NaH (865 mg, 36.0 mmol) in THF (200 mL) was treated with 6 (5.22 g, 30.0 mmol) at room temperature. When the evolution of gas had ceased, the mixture was stirred for 1 h before treating with p-toluenesulfonyl chloride (6.30 g, 33.0 mmol). After 16 h, the conversion was complete as monitored by TLC. The reaction mixture was quenched by adding aqueous NH4Cl. Ethyl acetate was added and the organic layer was separated. The organic layer was washed with water, brine and dried (Na2SO4). Concentration followed by crystallization (ethyl acetate/hexanes) afforded pale yellow crystals (6.75 g, 68%): mp 83-85° C.; 1H NMR δ 2.43 (s, 3H), 7.09 (d, J=2.0 Hz, 1H), 7.35 (d, J=8.3 Hz, 2H), 7.57 (d, J=2.0 Hz, 1H), 7.81 (d, J=8.3 Hz, 2H), 9.94 (s, 1H); 13C NMR δ 22.0, 101.8, 125.4, 127.8, 127.9, 130.6, 133.5, 134.7, 146.7, 178.5. Anal. Calcd or C12H10BrNO3S: C, 43.92; H, 3.07; N, 4.27; S, 9.77. Found: C, 43.92; H, 3.02; N, 4.26; S, 9.84.

出典