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

HRID 30825

Reaction equation

HRID 30825 reaction equation
[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]

Participants

10

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c0ef632ba96748608141c61764770d25
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Linked notes

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