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

HRID 30825

反応式

HRID 30825 の反応式
[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]

参加物

10

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0ef632ba96748608141c61764770d25
出典データセット
uspto-grants-2008_09
特許番号
US07423150B2

関連ノート

読み込み中…