Triethylamine → HCID 89975671, compound

HRID 716139Notes

Reaction equation

HRID 716139 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][N:10]=[CH:11][CH:12]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][CH:14]([OH:16])[CH3:15].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(OCC)(=O)C>O1CCCC1.O>[CH3:24][S:25]([O:16][CH:14]([CH2:13][CH:12]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:11]=[N:10][O:9][CH3:8])[CH3:15])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 89975670HCID 89975670, compound

Product 1

HCID 89975671HCID 89975671, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

3.3 mL of triethylamine was added to a solution of 3.6 g of 5-(methoxyimino)-4-phenoxypentan-2-ol in 36 mL of tetrahydrofuran, and thereafter, 1.2 mL of methanesulfonyl chloride was added to the mixture at a temperature of 0° C. to 10° C. The obtained mixture was stirred at 15° C. or lower for 1 hour. Thereafter, 200 mL of ethyl acetate and 200 mL of water were added to the reaction mixture, and the water layer was then removed. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), so as to obtain 4.4 g of 5-(methoxyimino)-4-phenoxypentan-2-yl methanesulfonate in the form of a light yellow oily product.

Workup

  1. customthe water layer was then removed
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-cfe32bd0d9e94edc8874ddf44b35beec
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

Loading…