18-Crown-6 → 4,4,4-Trimethoxybutyl para-toluenethiosulphonate

HRID 1611014Notes

Reaction equation

HRID 1611014 reaction equation
[K+].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8](=[S:11])([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]([O:22][CH3:23])([O:20][CH3:21])[CH2:16][CH2:17][CH2:18]Br.C1OCCOCCOCCOCCOCCOC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8](=[S:11])([O:10][CH2:18][CH2:17][CH2:16][C:15]([O:22][CH3:23])([O:20][CH3:21])[O:14][CH3:13])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 516892Sodium BicarbonateHCID 5187924Trimethyl 4-bromoorthobutyrateHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt

Product 1

HCID 537006924,4,4-Trimethoxybutyl para-toluenethiosulphonateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of para-toluenethiosulphonic acid potassium salt (8.77 g), trimethyl 4-bromoorthobutyrate (8.00 g) and 18-crown-6 (10.24 g) in anhydrous tetrahydrofuran (60 ml) was ultrasonicated for 5 minutes then stirred at room temperature for 3 days. The mixture was poured into saturated aqueous sodium bicarbonate solution (200 ml) and extracted with ether (2×200 ml). The organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the subtitle compound (10.52 g) as an oil.

Workup

  1. customwas ultrasonicated for 5 minutes
  2. extractionextracted with ether (2×200 ml)
  3. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-80d0f9893ed14f109989b4282515a231
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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