Acetone → HCID 54249333, compound

HRID 483653Notes

Reaction equation

HRID 483653 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.CC(C)=O.C(=O)([O-])[O-].[Ca+2]>C(Cl)Cl.O>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([F:32])[CH2:25][CH:26]=[O: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

7

Reactant 4

HCID 180AcetoneHCID 10112Calcium CarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 18652647HCID 18652647, compound

Product 1

HCID 54249333HCID 54249333, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the dithialane prepared in 3F (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 the expected aldehyde as an oil which was used after drying under high vacuum (0.366 g, 92%).

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

Sources & evidence

ORD record
ord-6e41c7f684144ba28495aa2c50e8a41b
Source dataset
uspto-grants-1993_07
Patent number
US05225429

Reaction notes

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