Lithium Hydroxide → 1-(5-Ethynyl-2-thienyl)-2,2,2-trifluoroethanone

HRID 1715350Notes

Reaction equation

HRID 1715350 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[C:10]([C:7]1[S:6][C:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:16])=[CH:9][CH:8]=1)#[CH:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 685070782,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone

Product 1

HCID 576201031-(5-Ethynyl-2-thienyl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of D1 (1.0 eq) in THF (0.1 M) at RT was added a solution of LiOH (2.0 eq) in H2O (0.1 M) and the reaction mixture was stirred for 1 hr, then quenched by adding 6M HCl solution until pH=2. The organic solvent was evaporated and the product was extracted by DCM. Organic layers were washed with brine and dried (Na2SO4). Evaporation of the solvent under reduced pressure gave the crude product which was purified by flash column chromatography using Pentane to yield the desired compound as a brown oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.85-7.80 (1H, m), 7.32 (1H, d, J=4.2 Hz), 3.66 (1H, s).

Workup

  1. customquenched
  2. additionby adding 6M HCl solution until pH=2
  3. customThe organic solvent was evaporated
  4. extractionthe product was extracted by DCM
  5. washOrganic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent under reduced pressure
  8. customgave the crude product which
  9. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-21d3111858bb4bc586bc5bdd9f69c1fe
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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