Diethyl Ether → HCID 19843669, compound

HRID 2352666Notes

Reaction equation

HRID 2352666 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=O)=O.S([C:16]1[CH:22]=CC(C)=C[CH:17]=1)([O-])(=O)=O.[OH-:23].[Na+].CC[O:27][CH2:28]C>N1C=CC=CC=1.[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.O>[CH3:28][O:27][CH2:5][CH2:6][CH2:7][CH2:9][CH2:10][CH2:4][S:1][CH2:17][CH:16]1[CH2:22][O:23]1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 85570p-Toluenesulfonate

Product 1

HCID 19843669HCID 19843669, compound

Reagents, catalysts & solvents 3

HCID 77620884Tricaprylylmethyl ammonium chlorideCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Tosyl chloride (3.6 g, 18.9 mmol) is added in portions to a solution of the above diol (4.2 g, 18.9 mmol) in 15 ml of pyridine at 0°-5°. The mixture is stirred at 0° for 1 hour, then is stirred at RT for 1 hour. The reaction is quenched with water; extracted with ether; washed with 2N H2SO4, water, saturated NaHCO3 and brine; and dried. The resulting tosylate (5.8 g, 17.4 mmol) is mixed with sodium hydroxide (0.69 g, 17.4 mmol), ether (20 ml) and water (25 ml), and to this mixture is added 3 drops of tricaprylylmethylammonium chloride (Aliquat 336, Aldrich). The mixture is stirred at RT for 4 hours, then extracted with ether, washed with brine and dried to give 2-(6-methoxyhexylthiomethyl)oxirane.

Workup

  1. stirringis stirred at RT for 1 hour
  2. customThe reaction is quenched with water
  3. extractionextracted with ether
  4. washwashed with 2N H2SO4, water, saturated NaHCO3 and brine
  5. customand dried
  6. stirringThe mixture is stirred at RT for 4 hours
  7. extractionextracted with ether
  8. washwashed with brine
  9. customdried

Sources & evidence

ORD record
ord-a384cc1138e24d89918727530dfae4f6
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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