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

HRID 855064

반응식

HRID 855064 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 67803Tetramethylammonium fluoride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd1be1d60e2d47369ff2eeafcd3216d2
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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