反応 #10320

反応方程式

4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol

1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one

Diethyl ether

sodium hydroxide

→

4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde

収率 88.6%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred vigorously for 15 minutes
2. 2
   洗浄The organic layer was washed with sodium hydroxide, water and brine
3. 3
   乾燥dried over MgSO4
4. 4
   その他evaporated in vacuo

実験手順

A solution of 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (Step 1, 320 mg, 1.9 mmol) in dichloromethane (10 mL) was added to a stirred solution of 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.92 g, 2.1 mmol) in dichloromethane (10 mL) under nitrogen and stirred at room temperature for 20 minutes. Diethyl ether (50 mL) and 1N sodium hydroxide solution (25 mL) were added and the mixture stirred vigorously for 15 minutes. The organic layer was washed with sodium hydroxide, water and brine, dried over MgSO4 and evaporated in vacuo to give 4,5,6,7-tetrahydro-1-benzothiophene-3-carbaldehyde (280 mg, 88%). 1H NMR (360 MHz, CDCl3) δ 9.88 (1H, s), 7.85 (1H, s), 2.92–2.88 (2H, m), 2.76 (2H, t, J=6.0 Hz), 1.88–1.76 (4H, m).

出典