Methanol → HCID 85126194, compound

HRID 1242271Notes

Reaction equation

HRID 1242271 reaction equation
[C:1]1([CH:7]([CH2:10][CH2:11][CH3:12])C=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([NH:17][OH:18])([CH3:16])([CH3:15])[CH3:14].[CH3:19]O>Cl>[C:13]([N+:17]([O-:18])=[CH:19][CH2:12][CH2:11][CH2:10][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 98586N-tert-butylhydroxylamineHCID 1471522821765-78-6

Product 1

HCID 85126194HCID 85126194, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

To a mixture of 5-[phenyl-pentanal (1.62 g, 10 mmol, 1.0 equiv) and methanol (50 ml) was added N-tert-butylhydroxylamine (0.93 g, 10.43 mmol, 1.25 equiv) followed by 10 drops of conc. HCl. The mixture was stirred at rt for 18 h. The mixture was concentrated under vacuum to yield a light colored oil. The residue oil was purified by column chromatography (hexane:EtOAc 1:1) followed by EtOAc to give the title compound as a lightly colored oil: Yield: 39%: 1H NMR (CDCl3) δ 7.20 (m, 5H), 6.94 (d, 1H), 2.50 (m, 4H), 1.60 (m, 4H), 1.46 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto yield a light colored oil
  3. customThe residue oil was purified by column chromatography (hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-2c1c737f7d56406caca5087ffa0a873c
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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