Benzyl Alcohol → HCID 22875681, compound

HRID 362798Notes

Reaction equation

HRID 362798 reaction equation
C(O)C1C=CC=CC=1.[Si:9]([O:16][CH:17]([C@@H:19]1[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@H:33]([CH2:34][CH2:35]2)[C@:31]2([CH3:32])[C:26](=[CH:27][C:28](=[O:38])[CH2:29][CH2:30]2)[CH:25]=[C:24]3[CH3:39])[CH2:21][CH2:20]1)[CH3:18])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>[Pd].CCCCCCC>[Si:9]([O:16][CH:17]([C@@H:19]1[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@H:33]([CH2:34][CH2:35]2)[C@:31]2([CH3:32])[C:26](=[CH:27][C:28](=[O:38])[CH2:29][CH2:30]2)[CH2:25][C@@H:24]3[CH3:39])[CH2:21][CH2:20]1)[CH3:18])([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 22875682HCID 22875682, compound2×

Product 1

HCID 22875681HCID 22875681, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8900HeptaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A slurry of 5% palladium on carbon (7.12 gm) and benzyl alcohol (213 mL) in heptane (356 mL) was refluxed for 20 min. The mixture was cooled to 80° C. and a solution of 20-tert-butyldimethylsilyloxy-7-methyl-pregn-4,6-dien-3-one (71.2 gm, 0.16 mol, product of Step 5) in heptane (427 mL) was added. The slurry was refluxed for 9.5 h. The reaction was cooled to room temperature and filtered through SOLKA FLOK filter aid which was subsequently washed with hexane. The filtrate was extracted with acetonitrile which was subsequently back-extracted with hexane. The heptane and hexane extracts were combined, washed with saturated sodium sulfate and saturated salt solutions, and dried over anhydrous magnesium sulfate. The solution was filtered through a pad of anhydrous sodium sulfate and the solvent removed by rotoevaporation. The title compound was purified by column chromatography on silica gel eluted with 7% ethyl acetate in hexanes.

Workup

  1. temperatureThe slurry was refluxed for 9.5 h
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered through SOLKA FLOK
  4. filtrationfilter aid which
  5. washwas subsequently washed with hexane
  6. extractionThe filtrate was extracted with acetonitrile which
  7. extractionwas subsequently back-extracted with hexane
  8. washwashed with saturated sodium sulfate and saturated salt solutions
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe solution was filtered through a pad of anhydrous sodium sulfate
  11. customthe solvent removed by rotoevaporation
  12. customThe title compound was purified by column chromatography on silica gel
  13. washeluted with 7% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ad5bc8a4ea9646fe89db376bfe8e444a
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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