Gamma-Valerolactone → 4-Hydroxy-pentanoic acid methoxy-methyl-amide

HRID 1988223Notes

Reaction equation

[CH3:1][CH:2]1[O:6][C:5](=[O:7])[CH2:4][CH2:3]1.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[O:13]([NH2:15])[CH3:14].[C:16](=O)(O)[O-].[Na+]>ClCCl>[CH3:14][O:13][N:15]([CH3:16])[C:5](=[O:7])[CH2:4][CH2:3][CH:2]([OH:6])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-methyl-dihydro-furan-2-one (0.2 m L, 2.1 m mol) in dichloromethane (10 mL) was added a mixture of AlCl3 (3.1 mL, 6.2 mmol) and methoxylamine hydrochloride (0.6 g, 6.2 mmol) in dichloromethane (20 mL). After 1.5 hours, the reaction was cooled to 0° C. and a saturated sodium bicarbonate solution (10 mL) was added slowly. Extraction and concentration afforded 4-hydroxy-pentanoic acid methoxy-methyl-amide as a clear oil (184 mg).

Workup

extractionExtraction and concentration

Sources & evidence

ORD record: ord-be0be33fab3f43d0b1541ccc9a69b876
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553979B2

Reaction notes

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