Calcium Carbonate → HCID 54329766, compound

HRID 1885637Notes

Reaction equation

HRID 1885637 reaction equation
F[B-](F)(F)F.C[O+:7]([CH3:9])C.[Si:10]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([F:41])=[CH:33][CH2:34]C1SCCCS1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Ca+2].[BH4-].[Na+].[Na]>C(Cl)Cl.C(O)C.C(O)(=O)C.CC(C)=O.O>[Si:10]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([F:41])=[CH:33][CH2:34][CH2:9][OH:7])([C:23]([CH3:25])([CH3:26])[CH3:24])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

11

Reactant 5

HCID 10112Calcium CarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 54411416HCID 54411416, compound

Product 1

HCID 54329766HCID 54329766, compoundYield 74%

Reagents, catalysts & solvents 5

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

Procedure

To a suspension of trimethyloxonium tetrafluoroborate (0.44 g, 2.97 mmoles) in dry methylene chloride (15 ml) was added at room temperature the dithialane prepared in 1I (1.45 g, 2.97 mmoles) and the mixture was stirred for 1 hr. Then a 9:1 mixture of acetone and water (5 ml) containing calcium carbonate (0.6 g, 5.94 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 extacted 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 (10 ml) and sodium borohydride (56 mg, 1.48 mmoles) was added. The mixture was stirred 30 min at 0° C. The excess of sodium boronhydride was reacted with acetone, the mixture was acidified with acetic acid and concentrated under reduced pressure. The residue was taken 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 28:72 mixture of ethyl acetate and hexane afforded the title alcohol as an oil (0.813 g, 74%). NMR (H1, CDCl3, 60 MHz) characteristic peaks: 1.06 (s, 9), 3.4 to 3.8 (m, 4), 5.0 (dt, JHF =21 Hz, JHH =8 Hz, 7.2 to 7.76 (m, 10).

Workup

  1. additionwas added at room temperature the dithialane
  2. additionwas added
  3. stirringthe mixture was stirred overnight at room temperature
  4. filtrationThe precipitate was filtered off
  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 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 28:72 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-448c9eb41c6149699be4bd46e5b24b13
Source dataset
uspto-grants-1992_09
Patent number
US05145861

Reaction notes

Loading…