Water → HCID 86758101, compound

HRID 2184667Notes

Reaction equation

HRID 2184667 reaction equation
[CH:1](=[N:8]/[OH:9])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrCC(O[C:15]([CH3:18])([CH3:17])[CH3:16])=O.[Na].[OH2:20].C[CH:22]([OH:24])[CH3:23]>>[C:15]([CH:23]([C:22]([OH:24])=[O:20])[N+:8]([O-:9])=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 5

HCID 962WaterHCID 3776IsopropanolHCID 79177tert-Butyl bromoacetateHCID 5324470Syn-benzaldehyde oximeHCID 5360545Sodium

Product 1

HCID 86758101HCID 86758101, compound

Procedure

Z-Benzaldoxime (5.64 g, 46.61 mmol) and t-butyl bromoacetate (7.58 mL, 10 g, 51.27 mmol) were added successively to a solution of sodium (1.07 g, 0.047 g-atom) in 2-propanol (120 mL). The suspension was stirred for 2 h and then poured into water (100 mL). Extraction with dichloromethane, followed by drying over anhydrous magnesium sulfate and concentration gave a residue which was chromatographed on silica gel. Elution with 60% ethyl acetate-hexanes gave t-butyl N-benzylideneglycine N-oxide.

Workup

  1. extractionExtraction with dichloromethane
  2. dry with materialby drying over anhydrous magnesium sulfate and concentration
  3. customgave a residue which
  4. customwas chromatographed on silica gel
  5. washElution with 60% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-20dd4b4f9dab4814971fc75f32f5e21f
Source dataset
uspto-grants-2002_06
Patent number
US06399600B1

Reaction notes

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