Lithium Hexamethyldisilazide → 4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

HRID 2395074Notes

Reaction equation

HRID 2395074 reaction equation
[Br-].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)([OH:4])=[O:3].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:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][CH:9]=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 133745943-(Benzyloxy)pyridine-2-carbaldehydeHCID 226755274-Carboxyphenethyltriphenylphosphonium bromide

Product 1

HCID 544494594-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (0.58 g, 1.17 mmol) was suspended in THF (7 ml) and lithium bis(trimethylsilyl)amide was added (1M in THF, 2.46 ml). The reaction mixture turned orange and was allowed to stir for 1 hour at ambient temperature. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (0.25 g, 1.17 mmol) in THF (3.5 ml) was added slowly. The reaction was stirred at ambient temperature for 1 hour. The reaction was quenched by the addition of water (8 ml) and ether (8 ml). The layers were separated, the ether layer was washed with water and the as aqueous layers were combined, acidified with 1N HCl and extracted with EtOAc (2×). The organic extracts were dried (MgSO4) and evaporated to give the title product as a mixture of isomers (2.7 g 66%).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 1 hour
  2. customThe reaction was quenched by the addition of water (8 ml) and ether (8 ml)
  3. customThe layers were separated
  4. washthe ether layer was washed with water
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-6441c0bbfdf043f2804789475f0dcf23
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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