Ethyl Acetate → 5α-Cholest-8(14)-en-3β-ol

HRID 1939113Notes

Reaction equation

HRID 1939113 reaction equation
[CH2:1]=[C:2]([CH:4]=[CH:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[H][H].C(OCC)(=[O:32])C>C(O)(=O)C.[Pt]=O>[CH3:8][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@H:16]([CH2:17][C@@H:18]([OH:32])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 71401261HCID 71401261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 52836655α-Cholest-8(14)-en-3β-ol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

50 g of cholestadiene were dissolved in 800 ml of dry ethyl acetate to which 30 ml of acetic acid had previously been added and after addition of 1.5 g of platinum oxide the mixture was transferred to an autoclave of 2 1 volume. Hydrogenation was carried out at 50° C. and 10 atm hydrogen pressure and was complete after 24 h. After reaction was complete, the catalyst was filtered off, the solvent was concentrated in a rotary evaporator and the doristerol obtained was recrystallized from ethanol. Yield: 42.5 g (88.5%). The purity of the substance was confirmed with the aid of 1H-NMR and 13C-NMR spectroscopy. 17 g of 4-(propen-2-oxy)benzoyl chloride and 32 g of doristerol were dissolved in 200 ml of dry toluene and heated to reflux for 15 h. The solvent was then distilled off and the residue was recrystallized from ethanol; yield: 44.9 g (99%), m.p. 92° C. (n*105i).

Workup

  1. additionhad previously been added
  2. customwas carried out at 50° C.
  3. customAfter reaction
  4. filtrationthe catalyst was filtered off
  5. concentrationthe solvent was concentrated in a rotary evaporator

Sources & evidence

ORD record
ord-687db4aad7be4b7cb773e80cad0b5af2
Source dataset
uspto-grants-1997_12
Patent number
US05695680

Reaction notes

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