Methanol → 5-(Hydroxymethyl)morpholin-3-one

HRID 1186385Notes

Reaction equation

HRID 1186385 reaction equation
CC(C)([O-])C.[Na+].Cl[CH2:8][C:9]([NH:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14])=[O:10].CO.O>C(O)(CC)(C)C>[OH:14][CH2:13][CH:12]1[NH:11][C:9](=[O:10])[CH2:8][O:16][CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23676156Sodium t-butoxideHCID 65312466HCID 65312466, compound

Product 1

HCID 250541545-(Hydroxymethyl)morpholin-3-oneYield 64%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

Sodium tert-butoxide (6.70 g, 59.7 mmol) was dissolved in tert-amyl alcohol (40 mL). To this, a tert-amyl alcohol solution (90 mL) of 2-chloro-N-(2-hydroxy-1-hydroxymethylethyl)acetamide (4.00 g, 23.9 mmol) was added dropwise at room temperature over 30 minutes, and the mixture was stirred at room temperature for 2 hours. To this, methanol (25 mL) and water (1.5 mL) were successively added and the mixture was further stirred at room temperature for 30 minutes. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=80/20) to give 5-(hydroxymethyl)morpholin-3-one (Compound EE) (2.00 g, yield: 64%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=80/20)

Sources & evidence

ORD record
ord-6a80091b0fc143b88fc4609388fb2e31
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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