Скачать или смотреть Alkylation of Alcohols, Part 1a: with Alkyl Halides and Sulfonates (mechanism, side reactions)

This video is about the mechanism and scope of the Williamson ether synthesis, that is, the alkylation of alkoxides by alkyl halides or sulfonates. Although most name reactions show a broad applicability and usually work well, the Williamson ether synthesis, unfortunately, does not. I'll give you therefore a large number of examples, but the presentation became too long for a single video and I've split it therefore into Part 1a and 1b.
Part 1a is about mechanism, scope, and side reactions of the Williamson ether synthesis. In Part 1b you can find many examples with detailed reaction conditions of the alkylation of primary, secondary, and tertiary alcohols, and of phenols.

Further examples:
Org. Proc. Res. Dev. 2020, 24, 1373-1392 (macrocyclization); 371-386 (ArOH); 2014, 18, 1142-1144 (RCH2OH, Et2SO4); 2013, 17, 257-264 (ROH, RCl); 2011, 15, 824-830 (ArOH); 2010, 14, 732-736 (ArOH, PTC); 716-721 (ROH, RCl, PTC); 2009, 13, 751-759 (ArOH, cyclic carbonate, Cs2CO3); 2005, 9, 749-756 (ArOH, RBr, PTC);
J. Org. Chem. 2019, 84, 4629-4638 (ArOH, ROMs); 2011, 76, 4260-4336 (tert-ROH); 2002, 43, 1187-1188 (ArOH); 1999, 40, 1843-1846 (ROH, CsOH);
Chem. Eur. J. 2019, 25, 16002-16006 (propargylation);
J. Med. Chem. 2017, 60, 4386-4402 (ROH, RBr, PTC);
WO 2016098128 (2016, ROH, RCl, KOH);
Tetrahedron Lett. 2016, 57, 4036-4038 (ROH, RCl, Cu-cat);
US 8957256 (2015, ROH, MeCl, NaOH);
J. Am. Chem. Soc. 2012, 134, 13415-13429 (ArOH, PTC);
WO 2009094457 (2009, clemastine);
US 2008-0021209 (2008, PTC);
Org. Lett. 2008, 10, 2453-2456 ((F3C)3COH);
Org. Prep. Proc. Int. 2004, 36, 380-383 (tartrates);
Tetrahedron: Asym. 2000, 11, 3619-3634 (ArOH);
WO 9936381 (1999, CF3CH2OH, NaOtBu, sulfonate);
Synthesis 1999, 94-99 (KOH);
US 5414142 (1995, no solvent);
Synthesis 1988, 560-562 (carbohydrates, KOH); 124-127 (glycosyl fluorides);
Org. Syn. 1998, 75, 37 (oxirane formation, KOH); 1990, 68, 92 (ROH, BnBr); 1981, 60, 92 (ROH, BnBr, Ag2O); 1974, 54, 19 (ROH, MeI); 1968, 48, 68 (KOMe, C5Cl6); 1955, 35, 59 (NaOEt, Cl2CHCO2H); 1952, 32, 68 (NaOEt, Cl3CNO2); 1942, 22, 56 (glucose, Ph3CCl); 1940, 20, 97 (glucose, Me2SO4); 1933, 13, 56 (Me2SO4); 42 (NaOEt, ClCH2CO2H), 1929, 9, 72 (PhONa, RCH2Br); 1926, 6, 48 (PhONa, RCH2Cl); 1925, 5, 55 (NaOEt, CHCl3).
Review: Org. Proc. Res. Dev. 2008, 12, 698-709 (PTC).