Hexane → HCID 13960148, compound

HRID 1607872Notes

Reaction equation

HRID 1607872 reaction equation
CCCCCC.C([Li])CCC.[CH3:12][S:13][CH:14]([S:17][CH3:18])[S:15][CH3:16].[OH:19][C@H:20]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[C:22](=[CH:23][CH2:24][C@@H:25]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:44])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[C@H:30]([CH3:35])[CH2:31][CH2:32][CH:33]=[O:34])[CH2:21]1>O1CCCC1>[OH:19][C@H:20]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[C:22](=[CH:23][CH2:24][C@@H:25]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:44])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[C@H:30]([CH3:35])[CH2:31][CH2:32][CH:33]([OH:34])[C:14]([S:17][CH3:18])([S:15][CH3:16])[S:13][CH3:12])[CH2:21]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 138491Methane, tris(methylthio)-HCID 10594587Chol-5-en-24-al-3(beta)-olHCID 178418339Butyllithium

Product 1

HCID 13960148HCID 13960148, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere at -78° C., 10.4 ml (17.7 mmoles) of a hexane solution of n-butyllithium was added to a solution of 2.4 ml (18.0 mmoles) of tris(methylthio)methane in 40 ml of tetrahydrofuran (THF for short), and the mixture was stirred for 40 minutes at the same temperature. To the mixture was added dropwise 15 ml of a THF solution of 798 mg (1.8 mmoles) of 3β-hydroxychol-5-en-24-al [compound of formula(VI)], and the mixture was stirred at -78° C. for 40 minutes. The mixture was extracted with ether in a customary manner, and the resulting residue was dissolved in a mixture of 10 ml of THF and 5 ml of methanol. Four drops of 2N hydrochloric acid was added, and the mixture was stirred at room temperature for 100 minutes. The mixture was extracted with ether in a customary manner, and the resulting crude product was purified by silica gel column chromatography [31 g; eluted with hexane/ethyl acetate (10:1)] to give 651 mg of the captioned compound having a melting point of141° to 143° C. (recrystallized from methanol).

Workup

  1. stirringthe mixture was stirred at -78° C. for 40 minutes
  2. extractionThe mixture was extracted with ether in a customary manner
  3. dissolutionthe resulting residue was dissolved in a mixture of 10 ml of THF and 5 ml of methanol
  4. additionFour drops of 2N hydrochloric acid was added
  5. stirringthe mixture was stirred at room temperature for 100 minutes
  6. extractionThe mixture was extracted with ether in a customary manner
  7. customthe resulting crude product was purified by silica gel column chromatography [31 g; eluted with hexane/ethyl acetate (10:1)]

Sources & evidence

ORD record
ord-885770f8aaca42a9b7f9be0e47ae8c45
Source dataset
uspto-grants-1989_09
Patent number
US04868165

Reaction notes

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