Hydrogen Peroxide → 5-propyl-6,7-dihydro-1-benzothiophen-4(5H)-one

HRID 1824126ノート

反応式

HRID 1824126 の反応式
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C(B(CC)CC)C.I[CH2:19][CH2:20][CH3:21].[OH-].[Na+].OO>O1CCCC1>[CH2:19]([CH:8]1[C:9](=[O:10])[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[CH2:6][CH2:7]1)[CH2:20][CH3:21]

参加物

7

反応物 5

HCID 784Hydrogen PeroxideHCID 7357TriethylboraneHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 834184,5,6,7-Tetrahydro-4-oxothionaphthene

生成物 1

HCID 221474915-propyl-6,7-dihydro-1-benzothiophen-4(5H)-one収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of KH (30%, 11.44 g) in tetrahydrofuran (160 ml) under N2 was added dropwise 6,7-dihydro-1-benzothiophen-4(5H)-one (8 g) in tetrahydrofuran (40 ml). After 30 min, a triethyl borane (97 ml, 1 M THF) solution was added dropwise over 5 min. After 10 min, iodopropane was and the reaction stirred for 16 h. The reaction mixture was cooled to 0° C. and 1 N NaOH (250 ml) and hydrogen peroxide (12 ml, 30%) was added. The reaction mixture stirred for 1 h and was extracted with 400 ml ethyl acetate. The organic layer was washed with saturated sodium thiosulfate, dried MgSO4, filtered and concentrated. MPLC chromatography on a biotage 40 L with 4% ethyl acetate/heptane provided the title compound as an oil (8.21 g, 80%): 1H NMR (300 MHz, CDCl3) δ) 7.40, 7.07, 3.15–3.01, 2.47, 2.32, 2.07–1.88, 1.53–1.30, 1.27, 0.99–0.88; HRMS (FAB) calcd for C11H14OS+H 195.0844, found 195.0835.

後処理

  1. waitAfter 10 min
  2. stirringThe reaction mixture stirred for 1 h
  3. extractionwas extracted with 400 ml ethyl acetate
  4. washThe organic layer was washed with saturated sodium thiosulfate, dried MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f320e87adab3445c9095121362c76b63
出典データセット
uspto-grants-2006_05
特許番号
US07041672B2

反応ノート

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