HCID 13960166, compound → HCID 13960169, compound

HRID 1607873Notes

Reaction equation

HRID 1607873 reaction equation
[F:1][C:2]([F:33])([CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([OH:32])[CH2:23][CH2:24]2)=[CH:19][CH:18]=3)[CH2:15][CH2:14]1)[CH3:12])[C:3]([OH:8])([CH2:6][CH3:7])[CH2:4][CH3:5]>C1C=CC=CC=1.C(O)C>[CH3:5][CH2:4][C:3]([OH:8])([C:2]([F:33])([F:1])[CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@@:30]2([CH3:31])[CH2:29][CH2:28][CH2:27]/[C:17](=[CH:18]\[CH:19]=[C:20]3\[CH2:21][C@@H:22]([OH:32])[CH2:23][CH2:24][C:25]\3=[CH2:26])/[C@@H:16]2[CH2:15][CH2:14]1)[CH3:12])[CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 13960166HCID 13960166, compound

Product 1

HCID 13960169HCID 13960169, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

9.3 mg of 24,24-difluoro-3β,25-dihydroxy-26,27-dimethylcholesta-5,7-diene was dissolved in a mixture of 90 ml of benzene and 40 ml of ethanol, and in anargon stream at 0° C., the solution was irradiated with ultra-violetlight for 7 minutes using a medium-pressure mercury lamp through a Vycor filter. Subsequently, the reaction mixture was heated under reflux for 1 hour in at atmosphere of argon. The solvent was evaporated under reduced pressure, and the resulting crude product was purified by thin-layer silica gel chromatography (developing solvent: benzene/ethyl acetate=10:1;developed four times) to give 2.6 mg of the captioned vitamin D3 derivative [the compound of formula (I) in which X is H].

Workup

  1. customin anargon stream at 0° C., the solution was irradiated with ultra-violetlight for 7 minutes
  2. filtrationfilter
  3. temperatureSubsequently, the reaction mixture was heated
  4. temperatureunder reflux for 1 hour in at atmosphere of argon
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting crude product was purified by thin-layer silica gel chromatography (developing solvent: benzene/ethyl acetate=10:1;developed four times)

Sources & evidence

ORD record
ord-fd680faf828740a295b3c4d385d812b8
Source dataset
uspto-grants-1989_09
Patent number
US04868165

Reaction notes

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