Benzene → HCID 136463147, compound

HRID 1834901Notes

Reaction equation

HRID 1834901 reaction equation
[NH2:1][C@@H:2]1[C:18](=[O:19])[N:4]2[CH:5]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[C:6]([CH3:9])=[CH:7][S:8][C@H:3]12.[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])[CH:27]=O)([CH3:23])([CH3:22])[CH3:21].C1C=CC=CC=1>O>[C:33]([C:30]1[CH:29]=[C:26]([CH:25]=[C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:31]=1[OH:32])[CH:27]=[N:1][C@@H:2]1[C:18](=[O:19])[N:4]2[CH:5]([C:10]([O:12][CH2:13][C:14]([Cl:15])([Cl:17])[Cl:16])=[O:11])[C:6]([CH3:9])=[CH:7][S:8][C@H:3]12)([CH3:35])([CH3:36])[CH3:34]

Participants

5

Reactant 3

HCID 241BenzeneHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 70623070HCID 70623070, compound

Product 1

HCID 136463147HCID 136463147, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.14 g. of 2,2,2-trichloroethyl 7β-amino-3-methyl-2-cephem-4-carboxylate and 1.3 g. of 3,5-di-tert.-butyl-4-hydroxybenzaldehyde in 60 ml. of benzene was refluxed for 1.5 hours in a vessel equipped with a water separator. After evaporation of the solvent, a small amount of cyclohexane was added to the residue. Insolubles were filtered off, and the filtrate was purified by a dry silica gel column chromatography (4.5 × 15 cm, eluent; ethyl acetate-cyclohexane, 1 : 10) to give the desired product.

Workup

  1. customAfter evaporation of the solvent
  2. additiona small amount of cyclohexane was added to the residue
  3. filtrationInsolubles were filtered off
  4. customthe filtrate was purified by a dry silica gel column chromatography (4.5 × 15 cm, eluent; ethyl acetate-cyclohexane, 1 : 10)

Sources & evidence

ORD record
ord-cfd1a2d333a5466a83813d36287a47d4
Source dataset
uspto-grants-1978_01
Patent number
US04071681

Reaction notes

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