(2-Chloro-3-pyridinyl)methanol synthesis
- Product Name:(2-Chloro-3-pyridinyl)methanol
- CAS Number:42330-59-6
- Molecular formula:C6H6ClNO
- Molecular Weight:143.57
36404-88-3
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42330-59-6
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Yield:42330-59-6 80%
Reaction Conditions:
with sodium tetrahydroborate in methanol; for 1.7 h;
Steps:
4-Chlorophenyl-2-chloropyrid-3-ylmethanol1-3 5a
General procedure: To a stirred solution of 4a (29.80 g, 118.22 mmol) in MeOH (500 mL) was added portionwise sodium borohydride (2.24 g, 59.17 mmol) over 15 minutes. Stirring was continued for 1.5 hr, where upon the solvents were removed in vacuo. Water (500 mL) was added and the mixture extracted with EtOAc (3 × 250 mL). The organic extracts were washed successively with water (500 mL) and brine (500 mL), combined and evaporated in vacuo. The crude product was sonicated with n-hexane and the pure product collected by filtration to give the alcohol 5a (26.82 g, 89%) as a beige powder.
References:
Roughley, Stephen D.;Browne, Helen;MacIas, Alba T.;Benwell, Karen;Brooks, Teresa;D'Alessandro, Jalanie;Daniels, Zoe;Dugdale, Sarah;Francis, Geraint;Gibbons, Ben;Hart, Terance;Haymes, Timothy;Kennett, Guy;Lightowler, Sean;Matassova, Natalia;Mansell, Howard;Merrett, Angela;Misra, Anil;Padfield, Anthony;Parsons, Rachel;Pratt, Robert;Robertson, Alan;Simmonite, Heather;Tan, Kiri;Walls, Steven B.;Wong, Melanie [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 2,p. 901 - 906] Location in patent:supporting information; experimental part
2942-59-8
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42330-59-6
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1452-94-4
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42330-59-6
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40134-18-7
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42330-59-6
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49609-84-9
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42330-59-6
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