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2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles

✍ Scribed by Francisco Alonso; Emilio Lorenzo; Miguel Yus

Book ID
104259137
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
217 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

The re~tion of the title compound (1) with an excess of lithium powd= and a catalytic amount of tmphth~ae (2.5%) in the presence of an eleetrophile IEI+=ButCHO, Et2CO, (CHz)~CO, PhCOMe, Me3SiCI] in TItF at -78 to -30"C, followed by treatment with a second eleet~phfle IE2*-=ButCHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, ButCOMe, But2CO, PhCH=NI~, Me3SiCl, D20] at -30"C to roan teml~maa-e leads, af~ hydrolysis, to the expected compounds 2. For carbonyl derivmives, compomlds 2 were successively hydroborated (BH3-THF) und oxidised [33% H202 and then PCC or RuCI2(PPh3)3] to give directly the corresponding perhydroforofuruns 4.

πŸ“œ SIMILAR VOLUMES

Straight and versatile synthesis of subs
Straight and versatile synthesis of substituted perhydrofuro[2,3-b]pyrans from 2-chloromethyl-3-(2-methoxyethoxy)propene
✍ Francisco Alonso; Emilio Lorenzo; Jaisiel MelΓ©ndez; Miguel Yus πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 291 KB

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)propene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E 1 ΒΌR 1 R 2 CO) in THF at 278 to 08C, followed by the addition of an epoxide [E 2 ΒΌR 3 R 4 C(O)CHR 5 ] at 0 to 208C leads,