تفاعل #1474597

معادلة التفاعل

chloromethylpivalate

18-crown-6

3-(3,5-dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-5-chloro-1 H-indole

potassium tert-butoxide

→

title compound

المردود 44.1%

3-(3,5-Dibromo-4-pivaloyloxymethoxy-benzylidene)-2-oxo-2,3-dihydro-5-chloro-1H-indole

المردود 44.1%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was heated to seventy degrees celsius
2. 2
   workup.STIRRINGstirred for three hours
3. 3
   ترشيحthen filtered while hot
4. 4
   workup.STIRRINGstirred overnight
5. 5
   أخرىThe resulting solids were collected on a filter
6. 6
   غسيلwashed with acetonitrile
7. 7
   أخرىdried under vacuum

الإجراء التجريبي

A solution of 3-(3,5-dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-5-chloro-1 H-indole (0.43 g, 1.0 mmol) in dry acetonitrile (20 mL) under nitrogen was treated with potassium tert-butoxide (0.12 g, 1.1 mmol) at room temperature. The resulting orange heterogenous mixture was treated with 18-crown-6 (0.053 g, 0.20 mmol) and stirred for 15 minutes before adding chloromethylpivalate (0.40 mL, 2.8 mmol). The reaction was heated to seventy degrees celsius, stirred for three hours then filtered while hot. The filtrate was allowed to cool to room temperature and stirred overnight. The resulting solids were collected on a filter, washed with acetonitrile and dried under vacuum to provide the title compound (0.24 g, 44%) as a mixture of E/Z isomers. 1H NMR (DMSO-d6): (mixture of E/Z isomers) δ10.93 (s, 1H), 10.87(s, 1H), 8.85 (s, 2H), 8.09 (s, 2H), 7.94 (s, 1H), 7.84 (d, 1H), 7.67 (s, 1H), 7.32-7.39 (m, 3H), 6.96 (d, 1H), 6.91 (d, 1H), 5.91 (s, 2H), 5.88 (s, 2H), 1.23 (s, 9H), 1.22 (s, 9H). MS (ES-): 542 (60) (M−1). Anal. Calcd for C21H18NO4ClBr2: C, 46.40; H, 3.34; N, 2.58. Found: C, 46.33; H, 3.30; N, 2.55.

المصدر