Lithium Hexamethyldisilazide → Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate

HRID 2395068Notes

Reaction equation

HRID 2395068 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:42]([O:49][C:50]1[C:51]([CH:56]=O)=[N:52][CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1COCC1>[CH2:42]([O:49][C:50]1[C:51]([CH:56]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)=[N:52][CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 133745943-(Benzyloxy)pyridine-2-carbaldehyde

Product 1

HCID 54224333Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(4-Methoxycarbonylbenzyl)triphenylphosphonium bromide (4.42 g, 9.00 mmol) was suspended in THF (50 ml) under argon. Lithium bis-(trimethylsilyl)amide (1M in THF, 10.8 ml) was added and the deep orange reaction was stirred at ambient temperature for 1 hour. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (2.0 g, 9.4 mmol) in THF (20 ml) was added and the reaction was stirred at ambient temperature for 2 hours 30 minutes. The reaction was partitioned between EtOAc/water, the aqueous phase was extracted with EtOAc, the organic layers were combined, dried (MgSO4) and evaporated. The residue was purified by chromatography (EtOAc/CH2Cl2) to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate as a yellow oil. (3.01 g) .

Workup

  1. customthe deep orange reaction
  2. stirringthe reaction was stirred at ambient temperature for 2 hours 30 minutes
  3. customThe reaction was partitioned between EtOAc/water
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography (EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-3bd17c98d0124be180b015f38f357d95
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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