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

HRID 1635775

Reaction equation

HRID 1635775 reaction equation
C[O-].[Na+].[CH2:4]([SH:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl[CH2:15][C:16]#[C:17][CH2:18][S:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].O>CO>[C:21]([O:23][CH3:24])(=[O:22])[CH2:20][S:19][CH2:18][C:17]#[C:16][CH2:15][S:13][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 150771-NonanethiolHCID 10198037Methyl 7-chloro-3-thia-5-heptynoateHCID 10942334Sodium Methoxide

Product 1

HCID 86758809Methyl 3,8-dithia-5-heptadecynoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

2 ml of a 30% solution of sodium methoxide in methanol were added to a solution of 2 ml of nonanethiol in a 20 ml methanol/5 ml THF mixture, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then added to a solution of 2 g of methyl 7-chloro-3-thia-5-heptynoate in 20 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 15 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 oil thus obtained was chromatographed on a silica gel column (CH2Cl2/heptane 85/15) providing 2.1 g of methyl 3,8-dithia-5-heptadecynoate in the form of an orange-colored oil (yield 64%).

Workup

  1. temperatureThe mixture was maintained
  2. temperatureThe mixture was maintained
  3. stirringunder stirring for 15 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 oil thus obtained
  10. customwas chromatographed on a silica gel column (CH2Cl2/heptane 85/15)

Sources & evidence

ORD record
ord-cbb5bae05aa14167bb6092383d6b7c50
Source dataset
uspto-grants-2003_01
Patent number
US06511670B1

Linked notes

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