Dichloromethane → Methyl 11-thioacetylundecanoate

HRID 653349

反応式

HRID 653349 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[C:16](O)(=[S:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.C(CC(C)(C)C)(C)C.C(OCC)(=O)C.O>[C:16]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[S:18])[CH3:17]

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 223913Methyl 11-bromoundecanoateHCID 178418634HCID 178418634、化合物

生成物 1

HCID 20195807Methyl 11-thioacetylundecanoate収率 94.3%

試薬・触媒・溶媒 4

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 109072,2,4-Trimethylpentane溶媒

実験手順

Compound 103 (17.8 g, 64 mmol), thioacetic acid (9.7 g, 9.0 ml, 128 mmol), methyltrioctylammonium chloride (0.5 g), cesium carbonate (25 g, 77 mmol), dichloromethane (95 ml) and water (95 ml) were stirred at room temperature for 15 h. The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane, 1:5). The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4) and concentrated. Distillation gave pure 104 (15.6 g, 89%) with b.p. 137°-139° (0.1 torr) and m.p. <25° (from isooctane). 1H-NMR (CDCl3, Me4Si) δ 3.67 (s, 3H, MeO), 2.86 (t, 2H, J=7.1 Hz, S--CH2), 2.32 (s, 3H, MeCO), 2.30 (t, 2H, J=7.7 Hz, CH2CO). 13C-NMR (CDCl3, Me4Si) δ 195.9, 174.1 (CO), 51.3, 34.0, 30.5, 29.4, 29.3, 29.2, 29.1, 29.0, 28.9, 28.7, 24.8.

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. distillationDistillation

出典と根拠

ORDレコード
ord-3528f137b40f4eca9c0a965cf04714e1
出典データセット
uspto-grants-1987_06
特許番号
US04675392

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