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

HRID 10224

反応式

HRID 10224 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

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).

後処理

  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

出典と根拠

ORDレコード
ord-68919c0526124ce58060d7db7429fb11
出典データセット
uspto-grants-2006_08
特許番号
US07094777B2

関連ノート

読み込み中…