(Trifluoromethyl)trimethylsilane → ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855064

反応式

HRID 855064 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)=[O:2].C[Si](C)(C)[C:25]([F:28])([F:27])[F:26]>C1COCC1.[F-].C[N+](C)(C)C>[CH3:22][C:5]1[CH:6]=[C:7]2[C:12](=[C:3]([CH:1]([OH:2])[C:25]([F:28])([F:27])[F:26])[CH:4]=1)[O:11][CH:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2

参加物

5

反応物 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 86599485ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 86599487ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate収率 116%

試薬・触媒・溶媒 2

HCID 67803Tetramethylammonium fluoride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

The aldehyde from Example 605a, Step 1 (2.0 g, 6.37 mmol) in THF (20 mL) was cooled to 0° C. and treated with 98% trimethyl(trifluoromethyl)silane (1.18 g, 8.28 mmol) and 15 mg tetramethylammonium fluoride. The reaction was allowed to warm to room temperature and stirred for overnight. The HF (48%, 0.24 mL) was added to the reaction and the reaction was stirred for 6 hours. After LCMS indicated that there was no starting material in the reaction, the reaction was quenched with water, extracted with ethyl acetate, washed with water, brine, dried over MgSO4, and concentrated in vacuo to give a yellow semisolid (2.84 g), which had suitable purity to use without further purification.

後処理

  1. additionThe HF (48%, 0.24 mL) was added to the reaction
  2. stirringthe reaction was stirred for 6 hours
  3. customin the reaction
  4. customthe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fd1be1d60e2d47369ff2eeafcd3216d2
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

関連ノート

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