Triethylborane → 2-(2-Fluoro-5-nitrophenyl)-2-methylpent-4-enal

HRID 30825

반응식

HRID 30825 반응식
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[Cl-].[Li+].[F:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=1[CH:32]([CH3:35])[CH:33]=[O:34].[CH2:36](O)C=C.C(N(CC)CC)C.C(B(CC)CC)C>C1COCC1.C(=O)(O)[O-].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=1[C:32]([CH3:36])([CH2:35][CH:1]=[CH2:2])[CH:33]=[O:34]

참가 물질

10

반응물 6

HCID 7357TriethylboraneHCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 866004382-(2-Fluoro-5-nitrophenyl)propanal

생성물 1

HCID 866004392-(2-Fluoro-5-nitrophenyl)-2-methylpent-4-enal

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of palladium acetate (0.1 eq), triphenylphosphine (0.2 eq), lithium chloride (1.0 eq) in THF were sequentially added 2-(2-fluoro-5-nitrophenyl) propanal (1.1 eq) in THF, allyl alcohol (1.0 eq), triethylamine (1.2 eq) and triethylborane (2.4 eq) under nitrogen at room temperature. Solution was allowed to stir for 2 h. Mixture was diluted with saturated solution of sodium bicarbonate, extracted with ethyl acetate. Organics were washed with brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex: 15% EtoAc) on silica to afford 2-(2-fluoro-5-nitrophenyl)-2-methylpent-4-enal.

후처리

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washOrganics were washed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customCrude product was purified

출처 및 근거

ORD 기록
ord-c0ef632ba96748608141c61764770d25
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423150B2

연결된 노트

불러오는 중…