Calcium Carbonate → HCID 54426729, compound

HRID 1885640Notes

Reaction equation

HRID 1885640 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([F:32])[CH2:25][CH:26]1SCCCS1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.C[O+:39](C)C.C(=O)([O-])[O-].[Ca+2].[BH4-].[Na+]>C(Cl)Cl.C(O)C.C(O)(=O)C.CC(C)=O.O>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([F:32])[CH2:25][CH2:26][OH:39])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

10

Reactant 4

HCID 10112Calcium CarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 4311764Sodium borohydride2×HCID 53748011HCID 53748011, compound

Product 1

HCID 54426729HCID 54426729, compoundYield 49%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the dithialane prepared in 2F (0.424 g, 0.86 mmoles) in dry methylene chloride (4 ml) was added at room temperature trimethyloxonium tetrafluoroborate (0.125 g, 0.86 mmoles) and the mixture was stirred for 1 hr. Then a 9:1 mixture of acetone and water (2 ml) containing calcium carbonate (0.172 g, 1.72 mmoles) was added and the mixture was stirred overnight at room temperature. The precipitate was filtered off and after dilution with saturated brine the mixture was extracted three times with ether. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. The resulting oil was dissolved in ethanol (5 ml) and sodium borohydride (19 mg, 0.50 mmoles) was added. The mixture was stirred for 30 min at 0° C. The excess of sodium borohydride was treated with acetone, the mixture was acidified with acetic acid and concentrated under reduced pressure. The residue was taken up with water and extracted three times with ether. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. Flash chromatography on silicagel and elution with a 25:75 mixture of ethyl acetate and hexane afforded the desired alcohol as an oil (0.168 g, 49%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. filtrationThe precipitate was filtered off
  4. extractionafter dilution with saturated brine the mixture was extracted three times with ether
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford an oil
  9. stirringThe mixture was stirred for 30 min at 0° C
  10. concentrationconcentrated under reduced pressure
  11. extractionextracted three times with ether
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customto afford an oil
  16. washFlash chromatography on silicagel and elution
  17. additionwith a 25:75 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-6ee21139f1964ac29b7cf59a2cd5921b
Source dataset
uspto-grants-1992_09
Patent number
US05145861

Reaction notes

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