Sodium Acetate → HCID 57803527, compound

HRID 2103048Notes

Reaction equation

HRID 2103048 reaction equation
[CH2:1]([C:3]1[C:15]([OH:16])=[C:14]([CH2:17][CH3:18])[CH:13]=[C:12]2[C:4]=1[C:5](=O)[CH2:6][C:7]1([O:11]2)[CH2:10][CH2:9][CH2:8]1)[CH3:2].Cl.[CH3:21][O:22][NH2:23].C([O-])(=O)C.[Na+]>CO>[CH3:21][O:22]/[N:23]=[C:5]1\[CH2:6][C:7]2([O:11][C:12]3[C:4]\1=[C:3]([CH2:1][CH3:2])[C:15]([OH:16])=[C:14]([CH2:17][CH3:18])[CH:13]=3)[CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 69053186HCID 69053186, compound

Product 1

HCID 57803527HCID 57803527, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutan]-4-one (400 mg), methoxyamine hydrochloride (385 mg), and sodium acetate (379 mg) in methanol (10 mL) was refluxed for 16 hours. The methanol was removed by distillation and the residue was treated with sodium bicarbonate solution and ethyl acetate. The organic phase was washed with water and brine. Evaporation and chromatography (silica gel, hexane-ethyl acetate, 3.5%) gave 310 mg of (E)-5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutan]-4-one O-methyl oxime. 1H-NMR (300 MHz, CDCl3) δ=6.62 (s, 1H), 4.61 (s, 1H), 4.01 (s, 3H), 3.08 (q, J=7.5 Hz, 2H), 3.01 (s, 2H), 2.61 (q, J=7.5 Hz, 2H), 2.30-1.65 (m, 6H), 1.30-1.20 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=150.5, 149.4, 146.2, 133.1, 128.0, 115.7, 115.4, 77.0, 62.0, 33.3, 33.0, 23.3, 21.2, 13.4, 12.2 ppm. MS (m/z)=290 (100, M+H+).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe methanol was removed by distillation
  3. additionthe residue was treated with sodium bicarbonate solution and ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. customEvaporation and chromatography (silica gel, hexane-ethyl acetate, 3.5%)

Sources & evidence

ORD record
ord-9586c3ce5d834051841eab64588866b1
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…