Cyclohexanone → HCID 54411424, compound

HRID 1764940Notes

Reaction equation

HRID 1764940 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=[O:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C1(=O)CCCCC1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].CC(C)([O-])C.[Al+3].CC(C)([O-])C.CC(C)([O-])C.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CC(CCC[C@H]([C@@H]1[C@]2(C)C(=C3[C@H](CC2)[C@]2(C)C(C[C@@H](O)CC2)=CC3)CC1)C)C>CC(C)=O>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH:15]=[C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][CH:18]([OH:28])[CH2:17]4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C:12](=[C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C:18](=[O:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

9

Reactant 6

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 68399Aluminum tert-butoxideHCID 2724130Cornforth reagentHCID 15871124HCID 15871124, compoundHCID 46840178HCID 46840178, compound

Product 2

HCID 54411424HCID 54411424, compoundHCID 57221694HCID 57221694, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Cholesta-5,8-dien-3-ol 1, which is synthesised as described in the literature [J. Lip. Res. 37, 1529, (1996)], can be oxidised in an Oppenauer reaction to give cholesta-4,8-dien-3-one 2 (scheme 1). In this reaction, the sterol is treated with a ketone like acetone, quinone or cyclohexanone in the presence of aluminum isopropoxide or aluminum tert-butoxide [e.g. J. Chem. Soc. Perkin 12667 (1994)]. The sterol can also be oxidised with pyridinium dichromate [vide Synth. Commun. 20 (1990), 1167]. The same oxidation reaction can be carried out with cholesta-5,8(14)-dien-3β-ol, which is also synthesised as described in the literature [J. Lip. Res. 37 (1996), 1529,] to give cholesta-5,8(14)-dien-3-one. For this ketone, a laborious synthesis is described in the literature [Bull. Soc. Chim. Fr. 2037, (1971)]. Cholesta-4,7-dien-3-one is synthesised according to literature procedures [Liebigs Ann. Chem. 542 (1939), 218,] (in scheme 1, the series with the Δ8-double bond are shown as an example, analogous reactions have to be performed in the Δ7- and Δ8(14)-series).

Workup

  1. customcan be oxidised in an Oppenauer reaction
  2. customIn this reaction
  3. customThe same oxidation reaction
  4. customis also synthesised

Sources & evidence

ORD record
ord-47d86211caf542649b2e2e085f5b7ecc
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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