Tetrahydrofuran → Methyl (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-YL)acetate

HRID 2079318Notes

Reaction equation

HRID 2079318 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.[CH2:13]1COCC1.[Si](C=[N+]=[N-])(C)(C)C>CO>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([O:10][CH3:13])=[O:9])[C:4](=[O:11])[O:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 10655203Methyl (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-YL)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid (15.8 g, 90.9 mmol) in a 3:1 mixture of THF:MeOH (100 mL) was cooled in an ice bath. After adding 2.0 M TMSCHN2 (50 mL, 100 mmol) the bath was removed, and the mixture was stirred at room temperature for 3 h. The solvent was evaporated, and the crude material was purified via silica gel chromatography using 0-50% EtOAc/hexanes to give methyl 2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetate. 1H NMR (400 MHz, CDCl3) d 4.73 (dd, J=6.6, 3.8 Hz, 1H), 3.74 (s, 3H), 2.95 (dd, J=17.0, 3.9 Hz, 1H), 2.81 (dd, J=17.0, 6.6 Hz, 1H), 1.63 (s, 3H), 1.57 (s, 3H) ppm.

Workup

  1. customwas removed
  2. customThe solvent was evaporated
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-69bc494b050a433c87720d91eb6f1909
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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