Water → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

HRID 1166074노트

반응식

HRID 1166074 반응식
C1(S[C:8]2([O:11][C:12]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][C:13]=3[CH:14]=[O:15])[CH2:10][CH2:9]2)C=CC=CC=1.[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].O>C1COCC1>[CH:8]1([O:11][C:12]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:16][C:13]=2[CH:14]=[O:15])[CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 962WaterHCID 11768624Lithium naphthalenideHCID 215840782-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde

생성물 1

HCID 215840762-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde수율 6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Freshly cut lithium metal (97 mg, 13.9 mmol) was added to a solution of naphthalene (1.77 g, 13.9 mmol) in THF (20 mL) and the mixture was sonicated at room temperature for 30 min. to produce a dark green solution of lithium naphthalenide. A solution of 2-(1-phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde (Description 1, 96 mg, 0.27 mmol) in THF (2 mL) was cooled to −78° C. and the solution of lithium naphthalenide in THF (2 mL) was added dropwise until the intense green colour persisted. The reaction was then stirred for 5 min., water (6 mL) was added and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate, the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (80:20), to give to give the title compound as a colourless oil (4 mg, 6%). 1H NMR (360 MHz, CDCl3) δ 0.86 (4H, m), 3.82-3.9 (1H, m), 7.42 (2H, m), 7.62 (1H, d, J=2.5 Hz), and 10.36 (1H, s).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with hexane/Et2O (80:20)
  6. customto give

출처 및 근거

ORD 기록
ord-4983f2512af54a66a5c6e06fc091ce07
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613765B1

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