2(3H)-Furanone, 3-(triphenylphosphoranylidene)- → alpha-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-gamma-butyrolactone

HRID 326682Notes

Reaction equation

HRID 326682 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=O)[N:6]=1)([CH3:4])[CH3:3].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:25]2[CH2:30][CH2:29][O:28][C:26]2=[O:27])C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=[C:25]2[CH2:30][CH2:29][O:28][C:26]2=[O:27])[N:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 971112(3H)-Furanone, 3-(triphenylphosphoranylidene)-HCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

Product 1

HCID 57100695alpha-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-gamma-butyrolactoneYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4,6-bis(1,1-dimethylethyl)-5-hydroxypyrimidine-2-carboxaldehyde (0.5 g, 2.1 mmol) and α-triphenylphosphoranylidene-γ-butyrolactone (Katsumi, et al. Chem. Pharm. Bull. [Japan] 1986, 34, 619) (0.95 g, 2.8 mmol) in 50 mL of toluene is warmed to 60° C. overnight. The toluene is evaporated and the residue purified by flash chromatography (silica, 20% EtOAc/hexane). Recrystallization from hexane gives 0.4 g (62%) of α-[[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-γ-butyrolactone, mp 158°-160° C.

Workup

  1. customThe toluene is evaporated
  2. customthe residue purified by flash chromatography (silica, 20% EtOAc/hexane)
  3. customRecrystallization from hexane

Sources & evidence

ORD record
ord-3389f5eb0fee4c6292b6cd6f5320e0c8
Source dataset
uspto-grants-1993_12
Patent number
US05270319

Reaction notes

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