Water → Methyl 3,8-dithia-5-docosynoate

HRID 1635772Notes

Reaction equation

HRID 1635772 reaction equation
C[O-].[Na+].[CH2:4]([SH:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl[CH2:20][C:21]#[C:22][CH2:23][S:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].O>CO>[C:26]([O:28][CH3:29])(=[O:27])[CH2:25][S:24][CH2:23][C:22]#[C:21][CH2:20][S:18][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 646771-TetradecanethiolHCID 10198037Methyl 7-chloro-3-thia-5-heptynoateHCID 10942334Sodium Methoxide

Product 1

HCID 15462714Methyl 3,8-dithia-5-docosynoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

460 μl of a 30% solution of sodium methoxide in methanol were added to a solution of 665 μl of tetradecanethiol in a 5 ml methanol/2 ml THF mixture, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then 0.47 g of methyl 7-chloro-3-thia-5-heptynoate in 5 ml of methanol was added, under an inert atmosphere. The mixture was maintained under stirring for 8 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The wax thus obtained was chromatographed on a silica gel column (CH2Cl2) providing 1.05 g of methyl 3,8-dithia-5-docosynoate in the form of an oil. (Quantitative yield).

Workup

  1. temperatureThe mixture was maintained
  2. temperatureThe mixture was maintained
  3. stirringunder stirring for 8 hours at room temperature
  4. extractionextracted 3 times with ethyl ether
  5. washThe combined organic phases were washed 3 times with water
  6. dry with materialwith a saturated aqueous solution of NaCl before being dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum in a rotary evaporator
  9. customThe wax thus obtained
  10. customwas chromatographed on a silica gel column (CH2Cl2)

Sources & evidence

ORD record
ord-8d964890ccdc4b3393a65f0ec58277f7
Source dataset
uspto-grants-2003_01
Patent number
US06511670B1

Reaction notes

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