تفاعل #1121762

معادلة التفاعل

NaH

6

4-Bromopyrrole-2-carboxaldehyde

p-toluenesulfonyl chloride

→

crystals

المردود 68.6%

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

المردود 68.6%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 16 h
2. 2
   أخرىThe reaction mixture was quenched
3. 3
   workup.ADDITIONby adding aqueous NH4Cl
4. 4
   workup.ADDITIONEthyl acetate was added
5. 5
   أخرىthe organic layer was separated
6. 6
   غسيلThe organic layer was washed with water, brine
7. 7
   تجفيفdried (Na2SO4)
8. 8
   تركيزConcentration
9. 9
   أخرىfollowed by crystallization (ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر