Isopyridoxal → HCID 13066945, compound

HRID 614392Notes

Reaction equation

HRID 614392 reaction equation
[CH2:1]([Li])CCC.[Br-].C1(C([PH3+])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:27][C:28]1[C:33]([OH:34])=[C:32]([CH2:35][OH:36])[C:31]([CH:37]=O)=[CH:30][N:29]=1>O1CCCC1>[CH3:27][C:28]1[C:33]([OH:34])=[C:32]([CH2:35][OH:36])[C:31]([CH:37]=[CH2:1])=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 440899IsopyridoxalHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 13066945HCID 13066945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

67 Ml. of n-butyl lithium (1.9 M in n-hexane) was run into a stirred suspension of triphenylmethylphosphonium bromide (42.7 g., 0.12 M) at room temperature in tetrahydrofuran (300 ml.) under nitrogen. To this stirred solution a solution of the 3,4α-di-O-isopropylidine derivative of 2-methyl-3-hydroxy-4-hydroxymethyl-5-formylpyridine (24.7 gm. 0.119 M) in tetrahydrofuran (300 ml.) was added dropwise over 1 hour. The reaction was aged 1 hour at room temperature and then refluxed for 4 hours.

Workup

  1. temperaturerefluxed for 4 hours

Sources & evidence

ORD record
ord-58cdfbf3682b4a688820773536797e3b
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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