Diethyl Ether → 4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxaldehyde

HRID 10224

반응식

HRID 10224 반응식
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([CH2:10][OH:11])=[CH:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(OCC)C.[OH-].[Na+]>ClCCl>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([CH:10]=[O:11])=[CH:2]1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 219783784,5,6,7-Tetrahydro-1-benzothien-3-ylmethanol

생성물 1

HCID 441227304,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxaldehyde수율 88.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  1. stirringthe mixture stirred vigorously for 15 minutes
  2. washThe organic layer was washed with sodium hydroxide, water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-68919c0526124ce58060d7db7429fb11
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

연결된 노트

불러오는 중…