Dichloromethane → Cyclamen aldehyde

HRID 424612Notes

Reaction equation

HRID 424612 reaction equation
[H-].[CH2:2]([Al+]CC(C)C)[CH:3](C)[CH3:4].[H-].[Al+3].[Na+].[H-].[H-].[H-].[CH2:17](Cl)Cl.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1.C[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(OCC)C.C1(C)C=CC=CC=1>[CH3:2][CH:3]([C:28]1[CH:27]=[CH:26][C:24]([CH2:20][CH:21]([CH:22]=[O:23])[CH3:17])=[CH:30][CH:29]=1)[CH3:4]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 21862873HCID 21862873, compound

Product 1

HCID 517827Cyclamen aldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

The acetal A can be reduced in a reduction reaction with a reducing agent, for example diisobutylaluminium hydride, sodium aluminium hydride or borane-THF complex, in diethyl ether, methylene chloride, THF, hexane, toluene or a mixture of the solvent mentioned, at a temperature of from −95° C. to −20° C. to give the aldehyde B.

Workup

  1. custommentioned, at a temperature of from −95° C. to −20° C.

Sources & evidence

ORD record
ord-00c7c7953afc4abe9ed3190a9570ea0a
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

Loading…