2-Benzyloxy-3-pyridinecarbaldehyde → 4-[3-(2-Benzyloxy-3-pyridyl)prop-2-enyl]benzoic acid

HRID 2395073Notes

Reaction equation

HRID 2395073 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].[CH2:32]([O:39][C:40]1[C:45]([CH:46]=O)=[CH:44][CH:43]=[CH:42][N:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([O:39][C:40]1[C:45]([CH:46]=[CH:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][CH:9]=2)=[CH:44][CH:43]=[CH:42][N:41]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 189739592-Benzyloxy-3-pyridinecarbaldehydeHCID 226755274-Carboxyphenethyltriphenylphosphonium bromide

Product 1

HCID 538770954-[3-(2-Benzyloxy-3-pyridyl)prop-2-enyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (10.9 g, 22.2 mmol) was suspended in THF (80 ml) and the flask was flushed with argon. Lithium bis(trimethylsilyl)amide (1M in THF, 48.8 ml) was added dropwise and the reaction stirred for 1 hour, becoming dark brown. A solution of 2-benzyloxy-3-pyridinecarbaldehyde (4.73 g, 22.2 mmol) in THF (20 ml) was added slowly. The reaction was stirred at ambient temperature for 18 hours (shielding from light alumimium foil). The reaction mixture was then partitioned between Et2O/water, the organic layer was washed with water and the aqueous layers were combined, acidified with HCl and extracted with EtOAc. The organic phase was dried (MgSO4) and evaporated and purified by colum chromtagraphy with MeOH/CH2Cl2 to give the title product.

Workup

  1. customthe flask was flushed with argon
  2. additionLithium bis(trimethylsilyl)amide (1M in THF, 48.8 ml) was added dropwise
  3. stirringThe reaction was stirred at ambient temperature for 18 hours (shielding from light alumimium foil)
  4. customThe reaction mixture was then partitioned between Et2O/water
  5. washthe organic layer was washed with water
  6. extractionextracted with EtOAc
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customevaporated
  9. custompurified by colum chromtagraphy with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1959a29c08ff49b081fea1b788f276ff
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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