Water → 1-(But-3-ynyloxy-methyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane

HRID 1197369Notes

Reaction equation

HRID 1197369 reaction equation
C([Li])CCC.[CH2:6]([C:9]12[CH2:16][S:15][CH:12]([S:13][CH2:14]1)[S:11][CH2:10]2)[CH2:7][CH3:8].Cl[CH2:18][O:19][CH2:20][CH2:21][C:22]#[CH:23].O>O1CCCC1>[CH2:20]([O:19][CH2:18][C:12]12[S:11][CH2:10][C:9]([CH2:6][CH2:7][CH3:8])([CH2:16][S:15]1)[CH2:14][S:13]2)[CH2:21][C:22]#[CH:23]

Participants

6

Reactant 4

HCID 962WaterHCID 14868932But-3-ynyl chloromethyl etherHCID 193734094-n-Propyl-2,6,7-trithiabicyclo[2.2.2]octaneHCID 178418339Butyllithium

Product 1

HCID 193732901-(But-3-ynyloxy-methyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (0.3 ml, 1.6M solution in hexane) was added to a solution of 4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane (0.1 g) in dry tetrahydrofuran (5 ml) at -70° C., under nitrogen. The solution was stirred for 30 minutes and but-3-ynyl chloromethyl ether (0.058 g) in dry tetrahydrofuran (2.0 ml) was added and the reaction mixture was allowed to warm to 20°. Water (10 ml) was added and the mixture was extracted with diethyl ether. The ethereal extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by chromatography on alumina, eluting with 1:10 dichloromethane:hexane saturated with ammonia. 1-(But-3-ynyloxymethyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane was obtained as a waxy solid (0.032 g).

Workup

  1. temperatureto warm to 20°
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on alumina
  6. washeluting with 1:10 dichloromethane

Sources & evidence

ORD record
ord-cd3131d53a25433bbffa9552a812bc5e
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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