Ammonium Chloride → (1-Hydroxymethylcyclopropyl)acetic acid methyl ester

HRID 2194765Notes

Reaction equation

HRID 2194765 reaction equation
[CH2:1]1[C:3]2([CH2:7][C:6](=[O:8])[O:5][CH2:4]2)[CH2:2]1.CN(C)C(=O)C.[CH3:15][O-:16].[Na+].[Cl-].[NH4+]>CO.O>[CH3:15][O:16][C:6](=[O:8])[CH2:7][C:3]1([CH2:4][OH:5])[CH2:1][CH2:2]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 102194025-Oxaspiro[2.4]heptan-6-oneHCID 10942334Sodium Methoxide

Product 1

HCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl esterYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of crude 5-oxa-spiro[2.4]heptan-6-one (2.24 g, ca. 20 mmol; prepared according to the method of EP 0 678 515 A1 (herein incorporated by reference in its entirety for all purposes): impurity is N,N-dimethyl acetamide) in anhydrous methanol (40 mL) in water bath, was added sodium methoxide (1.296 g, 24 mmol). After 15 min, ammonium chloride (2 g) was added and the mixture was stirred at room temperature for 30 min. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 5.8 g (47%) of (1-hydroxymethyl-cyclopropyl)-acetic acid methyl ester as a colorless oil. 1H-NMR (200 MHz, CDCl3) δ 0.47-0.61 (4H, m), 2.44 (2H, s), 2.55 (1H, t, J=5.6 Hz), 3.48 (2H, d, J=5.6 Hz), 3.69 (3H, s).

Workup

  1. customprepared
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-27358a581bcc400b95f02ad5c1ae5d7d
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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