Acetic Acid → HCID 14802187, compound

HRID 2350996Notes

Reaction equation

HRID 2350996 reaction equation
[Si]([O:8][C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])[S:14][C:13]=2[C:26]=1[CH3:27])(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1>[OH:8][C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])[S:14][C:13]=2[C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14802186HCID 14802186, compound

Product 1

HCID 14802187HCID 14802187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.6 g of 5-(5-t-butyldimethylsilyloxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)-2,2-dimethylpentanoic acid (prepared as described in Example 80), 14.2 g of tetrabutylammonium fluoride trihydrate and 4.9 g of acetic acid were dissolved in 50 ml of tetrahydrofuran, and the mixture was reacted for 20 hours at room temperature. The reaction mixture was then condensed by evaporation under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and dried over anhydrous sodium sulfate, after which the ethyl acetate was distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography. The title compound was obtained from the fraction eluted with a 9:1 by volume mixture of benzene and ethyl acetate.

Workup

  1. customthe mixture was reacted for 20 hours at room temperature
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationafter which the ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-529a0223766447c7a1854cf255511bbb
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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