Problem Set 3 (2009) Key

Problem Set 3 (2009) Key - 3 on alcohol 2 Ethanol cat H 2...

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UCLA Chemistry 30B Synthesis Problem Set – 3 KEY 1 2 3 4 5 6 7 8 9 OH OH OH OH OH O O O O N H O O NH 2 NH 2 NH 2 OH O O OH HO OH OH 10 OH OH OH OH OH 1) SOCl 2 2) excess NH 3 3) LiAlH 4 THF 1) H 2 CrO 4 H 2 O Acetone 2) SOCl 2 3) Acid + NaH 1) H 2 CrO 4 H 2 O Acetone 2) SOCl 2 3) excess NH 3 4) NaH + acid chloride 1) PBr 3 2) NaCN DMF 3) LiAlH 4 THF 1) PBr 3 2a) Mg Et 2 O b) O 3) Ms-Cl Pyr 4) excess NH 3 1) H 2 CrO 4 H 2 O Acetone 2) Ethanol cat. H 2 SO 4 1) H 2 CrO 4 H 2 O Acetone 1' ) PBr
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Unformatted text preview: 3 on alcohol 2) Ethanol cat. H 2 SO 4 2'a ) Mg Et 2 O b) ester from step 2. 1) PCC CH 2 Cl 2 2 a) BuLi Ph 3 PBu + Br-b) aldehyde 1' ) PBr 3 on alcohol 1) PCC CH 2 Cl 2 2' ) PPh 3 3' a) BuLi THF b) aldehyde 3a) OsO 4 b) NaHSO 3 H 2 O 1) PCC CH 2 Cl 2 3) MCPBA CH 2 Cl 2 4) NaOH H 2 O 2 a) BuLi Ph 3 PBu + Br-b) aldehyde...
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