Toluene → HCID 135968527, compound

HRID 2396072Notes

Reaction equation

HRID 2396072 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([NH2:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21](=[O:28])[CH2:22][C:23](=O)[CH:24](Br)[CH3:25].O1CCOCC1.C1(C)C=CC=CC=1>O>[CH3:19][O:20][C:21](=[O:28])[CH2:22][C:23]1[N:10]=[C:8]([C:7]2[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]([OH:14])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[O:9][C:24]=1[CH3:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 312751,4-DioxaneHCID 6165023,5-Ditert-butyl-4-hydroxybenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 135968527HCID 135968527, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-di-tert-butyl-4-hydroxybenzamide (16.0 g, 64.3 mmol), 4-bromo-3-oxopentanoic acid methyl ester (18.6 g, 64.26 mmol), dioxane (60mL), and toluene (600 mL) was refluxed for 5 days with continuous water removal (Dean Stark trap). Then, the volatiles were removed in vacuo and the residue was purified by flash chromatography on silica gel (eluting solvent: hexane/EtOAc 3/1) to give a brown viscous oil (11.2 g). Crystallization of the brown oil from ethyl ether (after cooling to 0° C.) gave a white solid (9.2 g, 40% yield), m.p. 121°-123° C.

Workup

  1. customThen, the volatiles were removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel (eluting solvent: hexane/EtOAc 3/1)

Sources & evidence

ORD record
ord-0a95d139b57c42d4b2661d9b59cd7e92
Source dataset
uspto-grants-1996_02
Patent number
US05491159

Reaction notes

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