Acetic Acid → HCID 13592050, compound

HRID 2350982Notes

Reaction equation

HRID 2350982 reaction equation
[Si]([O:8][C:9]1[C:10]([CH3:27])=[C:11]([CH3:26])[C:12]2[O:16][C:15]([CH3:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:14][C:13]=2[C:24]=1[CH3:25])(C(C)(C)C)(C)C.C(O)(=O)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:8][C:9]1[C:10]([CH3:27])=[C:11]([CH3:26])[C:12]2[O:16][C:15]([CH3:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:14][C:13]=2[C:24]=1[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14802172HCID 14802172, compound

Product 1

HCID 13592050HCID 13592050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of 5-t-butyldimethylsilyloxy-2,4,6,7-tetramethyl-2-phenyl-1,3-benzoxathiole were dissolved in 30 ml of tetrahydrofuran. Under a stream of nitrogen, 4.5 g of acetic acid and 12.9 g of tetrabutylammonium fluoride trihydrate were then added to the mixture. The reaction mixture was then allowed to react for 2 hours at room temperature. At the end of this time, the reaction mixture was poured into water, and the resulting precipitate was extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The resulting crude oily substance was subjected to silica gel column chromatography. The title compound was obtained from the portion eluted with a 1:1 by volume mixture of cyclohexane and benzene. It melted at 80°-81° C.

Workup

  1. customto react for 2 hours at room temperature
  2. extractionthe resulting precipitate was extracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-5bc0a2adaa6a44a7b0cfa511da1e27ee
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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