Benzene → 60965-80-2

HRID 2397955Notes

Reaction equation

HRID 2397955 reaction equation
C([O:9][C@@H:10]1[C@@:43]2([CH3:44])[C:14](=[CH:15][CH:16]=[C:17]3[C@@H:42]2[CH2:41][CH2:40][C@@:39]2([CH3:45])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:38])[CH2:23][CH2:24][CH:25]([O:29]C(=O)C2C=CC=CC=2)[CH:26]([CH3:28])[CH3:27])[CH2:13][C@@H:12]([O:46]C(=O)C2C=CC=CC=2)[CH2:11]1)(=O)C1C=CC=CC=1.C1C=CC=CC=1>O>[CH3:38][C@@H:22]([C@@H:21]1[C@@:39]2([CH3:45])[CH2:40][CH2:41][CH2:42]/[C:17](=[CH:16]\[CH:15]=[C:14]3\[CH2:13][C@@H:12]([OH:46])[CH2:11][C@H:10]([OH:9])[C:43]\3=[CH2:44])/[C@@H:18]2[CH2:19][CH2:20]1)[CH2:23][CH2:24][CH:25]([OH:29])[CH:26]([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 241Benzene2×HCID 54481229HCID 54481229, compound

Product 1

HCID 643738760965-80-2Yield 11.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 mg of 1α,3β,24-tribenzoyloxycholesta-5,7-diene was dissolved in 500 ml. of benzene, and the resulting solution was irradiated with ultraviolet rays in an atmosphere of argon at 10° C. for 2 minutes. After the reaction, isomerization was carried out for 2 hours in the argon atmosphere under reflux of benzene. After the reaction, most of the benzene was evaporated off at reduced pressure, and 2 ml. of 5% potassium hydroxide-methanol and 2 ml. of benzene were added to the residue. The mixture was maintained at room temperature for 28 hours in an atmosphere of argon to perform hydrolysis. The reaction product was diluted with water, and extracted with ethyl acetate. The ethyl acetate layer was repeatedly washed with water, and dried. The ethyl acetate was evaporated off at reduced pressure. The residue was subjected to the same separating and purifying procedure as in Example 20 to afford 1.9 mg of 1α,24-dihydroxycholecalciferol having the same properties as the product obtained in Example 20.

Workup

  1. customAfter the reaction, isomerization
  2. customAfter the reaction
  3. custommost of the benzene was evaporated off at reduced pressure, and 2 ml
  4. additionof benzene were added to the residue
  5. customhydrolysis
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was repeatedly washed with water
  8. customdried
  9. customThe ethyl acetate was evaporated off at reduced pressure
  10. customsame separating
  11. custompurifying procedure as in Example 20

Sources & evidence

ORD record
ord-7e9169e0d4014c0bbd4ed0cc729ec39e
Source dataset
uspto-grants-1977_05
Patent number
US04022891

Reaction notes

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