Methanol → HCID 118120854, compound

HRID 1508665Notes

Reaction equation

HRID 1508665 reaction equation
CO.Cl.[CH3:4][O:5][NH2:6].[CH3:7][CH:8]1[O:12][CH:11](O)[CH:10]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:9]1>C(N(CC)CC)C>[CH3:4][O:5][N:6]=[CH:11][CH:10]([S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:9][CH:8]([OH:12])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118108777HCID 118108777, compound

Product 1

HCID 118120854HCID 118120854, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

8.0 mL of methanol and 712 mg of O-methylhydroxylamine hydrochloride were added to 1.5 g of 5-methyl-3-(pyridin-2-ylsulfanyl)oxolan-2-ol, and thereafter, 1.1 mL of triethylamine was added dropwise to the mixture. The thus obtained mixture was stirred at room temperature for 2 hours. Thereafter, the solvent was distilled away under reduced pressure, 50 mL of ethyl acetate and 50 mL of water were then added to the residue, and the water layer was then removed. The organic layer was washed with a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/acetone=4/1), so as to obtain 1.74 g of 5-(methoxyimino)-4-(pyridin-2-ylsulfanyl)pentan-2-ol in the form of a colorless oily product.

Workup

  1. distillationThereafter, the solvent was distilled away under reduced pressure, 50 mL of ethyl acetate and 50 mL of water
  2. additionwere then added to the residue
  3. customthe water layer was then removed
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialwas then dried over anhydrous magnesium sulfate
  6. distillationAfter that, the solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/acetone=4/1)

Sources & evidence

ORD record
ord-3a0ee735cf3148e2a900789a2c726c82
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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