Nitrogen → HCID 54273405, compound

HRID 234731Notes

Reaction equation

HRID 234731 reaction equation
O[C:2]1([CH3:29])[CH:26]=[C:25]2[C@:20]([CH3:27])([CH2:21][CH2:22][CH2:23][CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:28])([CH2:17][CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1.CC(C)[O-:32].[Al+3].CC(C)[O-].CC(C)[O-].CC(=O)CC.N#N>C1(C)C=CC=CC=1>[CH3:29][C:2]1[C@@H:3]2[C@@H:19]([C@:20]3([CH3:27])[C:25]([CH:26]=1)=[CH:24][C:23](=[O:32])[CH2:22][CH2:21]3)[CH2:18][CH2:17][C@@:16]1([CH3:28])[C@H:4]2[CH2:5][CH2:6][C@@H:7]1[C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6569Methyl Ethyl KetoneHCID 11143Aluminum isopropoxideHCID 54073812HCID 54073812, compound

Product 1

HCID 54273405HCID 54273405, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 7-hydroxy-7-methylchol-5-en-24-oate (8) (2.0 g, 4.78 mmoles), aluminum isopropoxide (1.17 g, 5.72 mmoles), 2-butanone (8.6 ml, 96 mmoles) in toluene (40 ml) was heated at 80° in a N2 atmosphere for 6 hrs. About 15 ml of solvent was distilled from the reaction mixture at atmospheric pressure. Toluene (30 ml) was added, and the mixture was extracted with 3N HCl (2 times), H2O (3 times) and dried with MgSO4. Evaporation in vacuo gave 1.7 g of an orange oil that was purified by flash chromatography on silica gel with hexane-EtOAc (7:2 and 2:1 ) to give 0.62 g of pure 9 as a colorless syrup. NMR (CDCl3): δ0.76 (s, 3H, 18-Me); 0.94 (d, 3H, 20-Me); 1.08 (s, 3H, 19-Me); 3.67 (s, 3H, CO2Me); 5.59 (s, 1H, 4H); 5.95 (s, 1H, 6-H).

Workup

  1. distillationAbout 15 ml of solvent was distilled from the reaction mixture at atmospheric pressure
  2. additionToluene (30 ml) was added
  3. extractionthe mixture was extracted with 3N HCl (2 times), H2O (3 times)
  4. dry with materialdried with MgSO4
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-c101f9570f224e8d832caa6bf2ffc193
Source dataset
uspto-grants-1997_01
Patent number
US05595996

Reaction notes

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