反応 #653635

反応方程式

Acetyl chloride

10

2-(1′-Hydroxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione

→

11

収率 74.0%

2-(1′-Acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione

収率 74.0%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   温度the mixture was refluxed for 4 h
2. 2
   その他The organic layer was separated
3. 3
   洗浄washed with saturated NaHCO3 and water
4. 4
   その他dried
5. 5
   その他evaporated

実験手順

Acetyl chloride (1.1 g, 13.6 mmol) was added to a solution of 10 (2.0 g, 7.4 mmol) in 1,2-dichloroethane (100 mL) and the mixture was refluxed for 4 h. After this time, the solution was poured into ice water. The organic layer was separated, washed with saturated NaHCO3 and water, dried, and evaporated. The residue was subjected to column chromatography (silica gel, C6H6) to give 11 as a yellow solid (mp 174-176° C.) in a 74% yield: IR (KBr) 1645, 1655, 1724 (C═O) cm−1; 1H NMR (CDCl3) δ 1.68 (d, J=6.6 Hz, 3H, CHCH3), 2.13 (s, 3H, COCH3), 6.10-6.17 (q, J=6.6 Hz, 1H, CH), 7.53 (s, 1H, H-3), 7.63 (d, J=5.1 Hz, 1H, H-7), 7.68 (d, J=5.1 Hz, 1H, H-6); 13C NMR (CDC3): δ 21.0 (C-2-COCH3), 22.0 (C-2-CHCH3), 67.4 (C-2-CH), 123.4 (C-3), 126.6 (C-7), 133.6 (C-6), 154.0 (C-2), 169.8 (C-2-C═O), 174.4×2 (C-4, C-8); MS m/z 306 (M+); Anal. (C14H10O4S2) C, H.

出典