3-Butynyl p-toluenesulfonate synthesis
- Product Name:3-Butynyl p-toluenesulfonate
- CAS Number:23418-85-1
- Molecular formula:C11H12O3S
- Molecular Weight:224.28
121-44-8
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$9.00/5g
98-59-9
592 suppliers
$9.00/5g
927-74-2
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$6.00/5g
23418-85-1
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$32.60/1g
554-68-7
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$6.00/25g
Yield:23418-85-1 97%
Reaction Conditions:
in dichloromethane at 0 - 20; for 21 h;
Steps:
2
3-Butyn-1-ol (1.8 g, 25 mmol) was dissolved in methylene chloride (CH2CL2) (40 mL) and triethylamine (ET3N) (4.18 mL, 30 mmol). The solution was stirred at 0°C followed by addition of p-toluenesulfonyl chloride (5.05 g, 26.25 mmol). The reaction was allowed to warm to room temperature over a period of 1 hour and stirring was continued overnight. Thin layer chromatography (TLC) analysis (hexanes/ethyl acetate (EtOAc) 6: 1) after 20 hours of reaction showed a complete consumption OF 3-BUTYN-1-OL. The precipitated triethylamine HYDROCHLORIDC was filtered off and the filtrate washed with water (H20) (30 mL) and brine (30 mL). The organic layer was dried over sodium sulfate (NA2S04) and the solvent evaporated away to give 155 as a light-yellow oil (5.45 g, 97%). The crude oil was used without further purification; however, it could be purified on a silica gel column, first eluting with 8% EtOAc in hexanes followed by 40% EtOAc in hexanes.
References:
RIB-X PHARMACEUTICALS, INC. WO2004/29066, 2004, A2 Location in patent:Page/Page column 215
121-44-8
858 suppliers
$9.00/5g
98-59-9
592 suppliers
$9.00/5g
927-74-2
426 suppliers
$6.00/5g
23418-85-1
158 suppliers
$32.60/1g