Methanol → 6-(Hydroxymethyl)morpholin-3-one

HRID 1048851Notes

Reaction equation

HRID 1048851 reaction equation
CC(C)([O-])C.[K+].Cl[CH2:8][C:9]([NH:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15])=[O:10].CO.O>C(O)(CC)(C)C>[OH:15][CH2:14][CH:13]1[CH2:12][NH:11][C:9](=[O:10])[CH2:8][O:16]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13233120HCID 13233120, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 534019466-(Hydroxymethyl)morpholin-3-oneYield 91.8%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

To a stirred solution of potassium tert-butoxide (23.4 g, 299.4 mmol) in 200 mL tert-amyl alcohol at room temperature was added 2-chloro-N-(2,3-dihydroxypropyl) acetamide (Step-1 of Intermediate-9) (20 g, 119.6 mmol) in 460 mL tert-amyl alcohol for 2 h under nitrogen atmosphere. After one hour, MeOH (100 mL) and H2O (3 mL) were added and further stirred for 20 min. The reaction mixture was concentrated under vacuum and purified by flash chromatography on silica gel with MeOH/EtOAc (20:80) to give the title compound as a white solid (14.4 g). m/z 132.1

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by flash chromatography on silica gel with MeOH/EtOAc (20:80)

Sources & evidence

ORD record
ord-9d567468999448218b4af1949708f0d9
Source dataset
uspto-grants-2016_07
Patent number
US09382216B2

Reaction notes

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