Dichloromethane → Methyl 11-thioacetylundecanoate

HRID 653349

Reaction equation

HRID 653349 reaction equation
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]

Participants

9

Reactant 4

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

Product 1

HCID 20195807Methyl 11-thioacetylundecanoateYield 94.3%

Reagents, catalysts & solvents 4

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 109072,2,4-TrimethylpentaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3528f137b40f4eca9c0a965cf04714e1
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Linked notes

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