Potassium Carbonate → Methyl 16-iodo-4-thia-hexadecanoate

HRID 279425Notes

Reaction equation

HRID 279425 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][I:14].[SH:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[K+].[K+].CCCCCC.C(OCC)(=O)C>C(#N)C>[I:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18050Methyl 3-mercaptopropionateHCID 113392051,12-DiiodododecaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 22625147Methyl 16-iodo-4-thia-hexadecanoateYield 32.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,12-diiodododecane (2.66 g, 6.3 mmol) was dissolved in 20 mL acetonitrile. Methyl 3-mercaptopropionate (0.76 g, 6.3 mmol) and K2CO3 (1.1 g, 8 mmol) were added and the mixture was allowed to react at room temperature for 20 h. The mixture was acidified with ice-diluted HCl and the solution was extracted twice with ether (20 mL). The combined ether fractions were washed successively with dilute NaHCO3, water and brine, dried (MgSO4 and evaporated under reduced pressure. The product 1 (0.84 g, 32% yield) was isolated by column chromatography (hexane/ethyl acetate 9:1) and recrystallized in MeOH. TLC (hexane/ethyl acetate 9:1) Rf=0.4. Melting point=33° C. 1H-NMR δ1.4 (m, 20H, CH2), 2.52 (t, 2H, C(2)H2), 2.61 (t, 2H, C(5)H2), 2,79 (t, 2H, C(3)H2), 3.20 (t, 2H, C(16)H2), 3.71 (s, 3H, —COO—CH3).

Workup

  1. customto react at room temperature for 20 h
  2. extractionthe solution was extracted twice with ether (20 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-9bea57135b9243e182579fbd82ea4b81
Source dataset
uspto-grants-2002_03
Patent number
US06362352B1

Reaction notes

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