Water → HCID 86605490, compound

HRID 2103044Notes

Reaction equation

HRID 2103044 reaction equation
[CH2:1]([C:3]1[CH:15]=[C:14]2[C:6]([C:7](=O)[CH2:8][C:9]3([O:13]2)[CH2:12][CH2:11][CH2:10]3)=[C:5]([CH3:17])[C:4]=1[OH:18])[CH3:2].Cl.[CH3:20][O:21][NH2:22].C([O-])(=O)C.[Na+].O>CO>[CH3:20][O:21][N:22]=[C:7]1[C:6]2[C:14](=[CH:15][C:3]([CH2:1][CH3:2])=[C:4]([OH:18])[C:5]=2[CH3:17])[O:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 69056802HCID 69056802, compound

Product 1

HCID 86605490HCID 86605490, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-ethyl-6-hydroxy-5-methylspiro[chroman-2,1′-cyclobutan]-4-one (0.8 g), methoxyamine HCl salt (500 mg) and sodium acetate (300 mg) in MeOH (20 mL) was stirred at 80° C. overnight. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate was dried and evaporated. The residue was purified by silica gel column eluting with 10% ethyl acetate in hexane, giving 7-ethyl-6-hydroxy-5-methylspiro[chroman-2,1′-cyclobutan]-4-one O-methyl oxime (530 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate was dried
  3. customevaporated
  4. customThe residue was purified by silica gel column
  5. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b1361f9e1fd542afa27317726711793a
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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