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PCC
PCC
PCC
Jones
Jones
Jones
H2 Pd/C
H2 Pd/C
A) NaBH4, MeOH
B) H3O+
A) NaBH4, MeOH
B) H3O+
2 step
A) NaBH4, MeOH
B) H3O+
2 step
LAH, THF, H3O+
Strong
LAH, THF, H3O+
LAH, THF, H3O+
LAH, THF, H3O+
NH4Cl (aq)
NH4Cl (aq)
NH4Cl (aq)
A) THF
B) NH4Cl (aq)
A) THF
B) NH4Cl (aq)
A) THF
B) NH4Cl (aq)
DIBAL-H
DIBAL-H
DIBAL-H