Dichloromethane → Methyl 11-thioacetylundecanoate

HRID 653349

반응식

HRID 653349 반응식
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]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 223913Methyl 11-bromoundecanoateHCID 178418634HCID 178418634, 화합물

생성물 1

HCID 20195807Methyl 11-thioacetylundecanoate수율 94.3%

시약·촉매·용매 4

HCID 21218Trioctylmethylammonium chloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 109072,2,4-Trimethylpentane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-3528f137b40f4eca9c0a965cf04714e1
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675392

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