Water → HCID 76614991, compound

HRID 2103023Notes

Reaction equation

HRID 2103023 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=O.Cl.[NH2:19][OH:20].O>CO>[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[N:19][OH:20]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 69054367HCID 69054367, compound

Product 1

HCID 76614991HCID 76614991, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 g of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one and 0.91 g of hydroxylamine hydrochloride was dissolved in 5 mL of MeOH by way of brief heating. After all solids had dissolved, the solution was sealed in a microwave reaction vial and placed in a microwave reactor for 25 min at 125° C. The reaction was cooled to room temperature, added to H2O and extracted with EtOAc, washed with brine and dried over Na2SO4. Evaporation of solvent yielded 1.05 g of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one oxime as a pale yellow solid.

Workup

  1. dissolutionAfter all solids had dissolved
  2. customthe solution was sealed in a microwave reaction vial
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-2dc27c0b2ef240fabdfab031950f36ec
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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