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Draw the Structure of Compound number 2, 4, 5, and 6 BH - THF 1) Bra 2) NaOme HO=CLI DMSO 1) Buli 2) I(CH2),OTHP ТѕОН TUD 6 Meow PdBASO MOH quinoline \2-Tetrahydropyranyl/

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Answer: First step is hydroboration in presence of borane (BH3) which results in the formation of alcohol (2). This is followed by substitution with bromine. In presence of alkyl lithium coupling reaction occurs between alkyl lithium and alkyl halide (3). Resulting compound 4 first react with BuLi to give another alkyl lithium which undergoes similar coupling reaction with alkyl halide (I(CH2)7OTHP) to give 5. OTHP group act as protecting group for alcohol and deprotection can be done in presence of TsOH/MeOH giving the corresponding alcohol 6. Finally in presence of Lindlars catalyst, the alkyne group is reduced to give cis-alkene (7). (The structure of the compound number 2,4,5,6 and 7 is given in the reaction scheme below.)

BHYTHF OH i) Br2 ii) NaOMe (3) HCECLI i) BuLi ii) I(CH2)70THP TSOH MeOH H2 Pd/BaSO4 MeOH quinoline IM HH

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