Ethyl 6-oxaspiro[2.5]octane-1-carboxylate synthesis
- Product Name:Ethyl 6-oxaspiro[2.5]octane-1-carboxylate
- CAS Number:909406-74-2
- Molecular formula:C10H16O3
- Molecular Weight:184.23
130312-00-4
86 suppliers
$40.00/250 mg
1774-47-6
556 suppliers
$6.00/25g
909406-74-2
38 suppliers
$220.00/1g
Yield: 280 mg
Reaction Conditions:
Stage #1:trimethylsulfoxonium iodide with sodium hydride in dimethyl sulfoxide;mineral oil at 0 - 20; for 0.333333 h;
Stage #2:ethyl tetrahydro-4H-pyran-4-ylideneacetate in dimethyl sulfoxide;mineral oil at 20; for 18 h;
Steps:
A solution of trimethylsulfoxonium iodide (800 mg, 3.63 mmol) and NaH (60% in mineral oil, 153 mg, 6.37 mmol) in DMSO (10 mL) was stirred at 0 °C to RT for 20 minutes. Then the reaction mixture was cooled to 0 °C and ester B-5a (500 mg, 2.94 mmol) in DMSO (5 mL) was added and stirred at RT for 18 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2x50 mL). The organic layer was washed with water (2x50 mL), brine (50 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (Silica gel 60-120, 10-15% EtO Ac/petroleum ether) to obtain ester B-6a (280 mg) as color less liquid.XH NMR (CDC13, δ = 7.26 ppm, 400 MHz): δ 4.13 (q, J = 7.2, 2 H), 3.74-3.56 (m, 4 H), 1.77-1.73 (m, 2 H), 1.56-1.42 (m, 3 H), 1.27 (t, J = 7.2, 3H), 1.17-1.15 (m, 1 H), 0.93-0.88 (m, 1 H).
References:
BRISTOL-MYERS SQUIBB COMPANY;HEWAWASAM, Piyasena;LOPEZ, Omar D.;TU, Yong;WANG, Alan Xiangdong;XU, Ningning;KADOW, John F.;MEANWELL, Nicholas A.;GUPTA, Samayamunthula Venkata Satya Arun Kumar;KUMAR, Indasi J. Gopi;PUNUGUPATI, Suresh Kumar;BELEMA, Makonen WO2015/5901, 2015, A1 Location in patent:Page/Page column 625
130312-00-4
86 suppliers
$40.00/250 mg
909406-74-2
38 suppliers
$220.00/1g
130312-00-4
86 suppliers
$40.00/250 mg
1030268-24-6
0 suppliers
inquiry
909406-74-2
38 suppliers
$220.00/1g
29943-42-8
433 suppliers
$5.00/1g
909406-74-2
38 suppliers
$220.00/1g