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

HRID 1715350ノート

反応式

HRID 1715350 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-21d3111858bb4bc586bc5bdd9f69c1fe
出典データセット
uspto-grants-2010_09
特許番号
US07799825B2

反応ノート

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