Tetrabutylammonium Fluoride → HCID 53807626, compound

HRID 330331Notes

Reaction equation

HRID 330331 reaction equation
CC([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[CH:25]=[CH:24][C:18]3[O:19][C:20]([F:23])([F:22])[O:21][C:17]=3[CH:16]=2)=[O:14])=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:23][C:20]1([F:22])[O:19][C:18]2[CH:24]=[CH:25][C:15]([C:13]([C:10]3[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=3)=[O:14])=[CH:16][C:17]=2[O:21]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70360188HCID 70360188, compound

Product 1

HCID 53807626HCID 53807626, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.4 grams (0.029 mole) of [4-[(1,1dimethylethyl)dimethylsilyloxy]phenyl](2,2-difluoro-1,3-benzodioxol-5-yl) ketone in 50 mL of tetrahydrofuran was stirred, and 13.7 grams (0.044 mole) of tetrabutylammonium fluoride was added. Upon completion of addition the reaction mixture was stirred for ten minutes. After this time the reaction mixture was washed in turn with an aqueous solution saturated with ammonium chloride, water, aqueous dilute hydrochloric acid, and an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 8.0 grams of 4-hydroxyphenyl (2,2-difluoro-1,3-benzodioxol-5-yl) ketone. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. washAfter this time the reaction mixture was washed in turn with an aqueous solution saturated with ammonium chloride, water, aqueous dilute hydrochloric acid
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-16bb6ae1f19842e88e471cc6c92b7bda
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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