تفاعل #10320

معادلة التفاعل

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

المردود 88.6%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture stirred vigorously for 15 minutes
2. 2
   غسيلThe organic layer was washed with sodium hydroxide, water and brine
3. 3
   تجفيفdried over MgSO4
4. 4
   أخرىevaporated in vacuo

الإجراء التجريبي

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).

المصدر