Acetic Acid → HCID 86759793, compound

HRID 584156Notes

Reaction equation

HRID 584156 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:47]=[CH:46][C:25]([O:26][CH2:27][C:28](=[O:45])[CH:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:34][CH:33]=2)[CH3:30])=[CH:24][CH:23]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][CH2:27][C:28](=[O:45])[CH:29]([O:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])=[CH:36][CH:37]=2)[CH3:30])=[CH:46][CH:47]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22345515HCID 22345515, compound

Product 1

HCID 86759793HCID 86759793, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (3R and 3S)-1-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-3-[4-(tert-butoxycarbonyl)phenoxy]-2-butanone (2.82 g, 4.32 mmol) in tetrahydrofuran (70 ml) was treated with acetic acid (1.5 ml) followed by 1M tetrabutylammonium fluoride in tetrahydrofuran (10 ml, 10.0 mmol). The mixture was then heated at 70° C. for 3.5 hours. The cooled mixture was then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 8:2) gave 1.64 g (91%) of the title material as an oil.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried (magnesium sulfate)
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 8:2)

Sources & evidence

ORD record
ord-eddb7ed278d3430e8858e8de9744942f
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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