Water → HCID 67517832, compound

HRID 511745Notes

Reaction equation

HRID 511745 reaction equation
CC(C)(C)C([O:5][CH:6]1[CH:13]2[CH:9]([CH2:10][CH:11]([CH:14]=O)[CH2:12]2)[C:8](=[O:16])[CH:7]1[C:17]1[C:22]([CH2:23][CH3:24])=[CH:21][C:20]([CH3:25])=[CH:19][C:18]=1[CH2:26][CH3:27])=O.C([O-])=O.[Na+].Cl.[NH2:35]O.O>C(O)=O.C(OCC)(=O)C>[CH2:26]([C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH2:23][CH3:24])[C:17]=1[CH:7]1[C:6](=[O:5])[CH:13]2[CH:9]([CH2:10][CH:11]([C:14]#[N:35])[CH2:12]2)[C:8]1=[O:16])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 86702735HCID 86702735, compound

Product 1

HCID 67517832HCID 67517832, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.91 g (2.30 mmol) of 2-(2,6-diethyl-4-methylphenyl)-5-formyl-3-oxooctahydropentalen-1-yl 2,2-dimethylpropanoate (Example I-b-2), 0.78 g (11.48 mmol) of sodium formate and 0.80 g (11.48 mmol) of hydroxylamine hydrochloride in 30 ml of formic acid are heated at reflux for 72 h. 50 ml of water are then added, and the mixture is stirred at room temperature for 1 h, taken up in ethyl acetate, washed twice with water, dried (magnesium sulphate) and concentrated using a rotary evaporator. The residue is chromatographed on silica gel (mobile phase ethyl acetate/hexane 1:6). This gives 0.31 g (44%) of the desired compound as a colourless oil.

Workup

  1. temperatureat reflux for 72 h
  2. washwashed twice with water
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customThe residue is chromatographed on silica gel (mobile phase ethyl acetate/hexane 1:6)

Sources & evidence

ORD record
ord-fa551dfb510142d18912a99523380234
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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