Methyl iodide → 5-methyl-6,7-dihydro-1-benzothiophen-4(5H)-one

HRID 1612195ノート

反応式

HRID 1612195 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.[CH:11]([N-]C(C)C)(C)C.[Li+].IC.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:11][CH:8]1[C:9](=[O:10])[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[CH2:6][CH2:7]1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 154115085-methyl-6,7-dihydro-1-benzothiophen-4(5H)-one収率 32%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6,7-dihydro-1-benzothiophen-4(5H)-one (1.63 g) in tetrahydrofuran (90 ml) at −78° C. under N2 was added lithium diisopropyl amide (5.89 ml, 2 M). After 30 min, iodomethane (0.732 ml) was added and the reaction was allowed to warm to ambient temperature. After 2 h, the reaction mixture was poured into saturated sodium bicarbonate (100 ml), extracted methylene chloride (3×100 ml), dried MgSO4, filtered and concentrated. MPLC was run on a biotage 40M column with 4-6% ethyl acetate/heptane to provide the title compound as an oil (560 mg, 32%): 1H NMR (300 MHz, CDCl3) δ) 7.41, 7.08, 3.15-2.99, 2.61-2.53, 2.33-2.25, 2.06-1.92, 1.28; HRMS (FAB) calcd for C9H10OS+H 167.0531, found 167.0527.

後処理

  1. waitAfter 2 h
  2. extractionextracted methylene chloride (3×100 ml), dried MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-eadb6f9c078a40e7a2aeebad10f3073c
出典データセット
uspto-grants-2006_01
特許番号
US06992087B2

反応ノート

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