Potassium Carbonate → HCID 22625144, compound

HRID 279430Notes

Reaction equation

HRID 279430 reaction equation
BrC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH3:13].[SH:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].[C:22]([O-])([O-])=O.[K+].[K+].CCCCCC.CCOCC>C(#N)C>[OH:14][CH:11]([CH2:12][CH2:13][CH3:22])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][S:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18050Methyl 3-mercaptopropionateHCID 10706786HCID 10706786, compoundHCID 21584099Diethylether hexane

Product 1

HCID 22625144HCID 22625144, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 12-bromo-3-dodecanol (8.78 g, 33.1 mmol) in acetonitrile (80 mL) was added methyl 3-mercaptopropionate (3-98 g. 33.1 mmol) and K2CO3 (5,5 g, 40 mmol). The mixture was allowed to react at room temperature for 20 hr. The mixture was acidified with ice-diluted HCl and the solution was extracted twice with ether (40 mL). The combined ether fractions were washed successively with dilute NaHCO3, water and brine, dried (MgSO4) and evaporated under reduced pressure. The product 7 (4.4 g, 44% yield) was isolated by column chromatography (hexane/ether 1:1) and recrystallized in hexane. TLC (hexane/ether 1:1) Rf=0.4. Melting point=38.8° C. 1H-NMR δ0.93 (t, 3H, C(16)H2), 1.4 (m, 18H, CH2), 2.52 (t, 2H, C(2)H2), 2.61(t, 2H, C(5) H2), 2.79 (t, 2H, C(3)H2), 3.60 (m, 1H, C(13)H), 3.70 (s, 3H,—COO—CH3).

Workup

  1. customto react at room temperature for 20 hr
  2. extractionthe solution was extracted twice with ether (40 mL)
  3. washThe combined ether fractions were washed successively with dilute NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-17cbd9be05de475e89f1fa9691c78d55
Source dataset
uspto-grants-2002_03
Patent number
US06362352B1

Reaction notes

Loading…