تفاعل #9796

معادلة التفاعل

ethyl 2-bromo-2-methylpropanate

intermediate 4

ethyl(4-mercapto-2-methylphenoxy)acetate

K2CO3

→

Intermediate 5

المردود 159.0%

ethyl(4-acetyl-2-methylphenoxy)acetate

المردود 159.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction cooled to rt
2. 2
   أخرىthe solvent removed in vacuo
3. 3
   workup.ADDITIONThe residue treated with water (200 mL)
4. 4
   استخلاصextracted 3×50 mL CH2Cl2
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   أخرىthe solvent removed under vaccum
8. 8
   أخرىThe residue was chromatographed (CH2Cl2/MeOH: 99/1)

الإجراء التجريبي

To intermediate 4 (710 mg, 1.81 mmol) in DMF (50 mL) was added the K2CO3 (275 mg, 1.99 mmol) followed by the ethyl 2-bromo-2-methylpropanate (280 μL, 1.91 mmol; Aldrich) and the reaction heated to 80° C. After 18 h, the reaction cooled to rt and the solvent removed in vacuo. The residue treated with water (200 mL), extracted 3×50 mL CH2Cl2, dried over Na2SO4, filtered and the solvent removed under vaccum. The residue was chromatographed (CH2Cl2/MeOH: 99/1). To afford 680 mg (77%) of Intermediate 5 as a clear oil. 1H NMR(CDCl3): δ 7.95 (d, 2H), 7.60 (d, 2H), 7.15 (d, 2H), 6.75 (d, 2H), 6.05 (t, 1H), 4.45 (d, 2H), 4.15 (q, 2H), 2.65 (s, 3H), 1.50 (s, 6H), 1.20 (t, 3H).

المصدر