Tetrabutylammonium Fluoride → 1-Ethynyl-4-(methoxymethoxy)-2-methylbenzene

HRID 631172Notes

Reaction equation

HRID 631172 reaction equation
C([Si](CC)(CC)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][CH3:15])=[CH:8][C:7]=1[CH3:16])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][CH3:15])=[CH:8][C:7]=1[CH3:16])#[CH:4]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67065522Triethyl((4-(methoxymethoxy)-2-methylphenyl)ethynyl)silane

Product 1

HCID 581665151-Ethynyl-4-(methoxymethoxy)-2-methylbenzene

Procedure

To a solution of triethyl((4-(methoxymethoxy)-2-methylphenyl)ethynyl)silane (1.0 equiv.) at 0° C. was slowly added tetrabutylammonium fluoride (1M solution in THF, 0.20 equiv.). At this point, the ice-bath was removed and the reaction mixture was allowed to stir at room temperature for 45 minutes. The reaction mixture was then passed through a pad of silica (packed with hexane) and eluted with 20% EtOAc in Hexanes to remove insoluble salts. The crude product was then purified by Combiflash using 0-10% EtOAc in Hexanes to give 1-ethynyl-4-(methoxymethoxy)-2-methylbenzene (8) as a slightly brown liquid.

Workup

  1. customat 0° C.
  2. customAt this point, the ice-bath was removed
  3. washeluted with 20% EtOAc in Hexanes
  4. customto remove insoluble salts
  5. customThe crude product was then purified by Combiflash

Sources & evidence

ORD record
ord-2c519dc34c1e46e194007fcafd77ed1f
Source dataset
uspto-grants-2016_04
Patent number
US09320748B2

Reaction notes

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