반응 #1102849

반응 방정식

sodium chlorite

sodium dihydrogenphosphate

3-Formyl-5-phenyl-thiophene-2-carboxylic acid tert-butyl ester

methyl sulfide

→

5-Phenyl-thiophene-2,3-dicarboxylic acid 2-tert-butyl ester

수율 100.0%

용매

water

THF

반응 조건

후처리

1. 1
   workup.ADDITIONadded over 1 min via a syringe
2. 2
   추출extracted with EtOAc (4×40 ml)
3. 3
   기타The aqueous phase was separated
4. 4
   추출extracted with more EtOAc (40 ml)
5. 5
   세척the combined extracts were washed with brine
6. 6
   기타dried
7. 7
   농축concentrated

실험 절차

A solution of 3-Formyl-5-phenyl-thiophene-2-carboxylic acid tert-butyl ester (300 mg, 1.04 mmol) in dry THF (20 ml), at 0° C., under nitrogen, was treated with methyl sulfide (10% w/w in THF, 3.8 ml, 5.2 mmol) followed by sodium dihydrogenphosphate (30% aqueous solution, 9.56 ml, 2.05 mmol). After 0.5 h, the solution was treated with sodium chlorite (30% w/w aqueous solution, 1.9 ml, 2.08 mmol) added over 1 min via a syringe. The pale yellow solution was stirred for 1.5 h at 0° C., then diluted with water (20 ml) and extracted with EtOAc (4×40 ml). The aqueous phase was separated, extracted with more EtOAc (40 ml) and the combined extracts were washed with brine dried and concentrated to give 316 mg (100%) of 5-Phenyl-thiophene-2,3-dicarboxylic acid 2-tert-butyl ester as a pale brown solid. NMR 1H (CD3CO; 400 MHz): 7.87 (s, 1H); 7.83-7.81 (m, 2H); 7.17-7.53 (m, 3H); 1.65 (bs, 9H).

출처