Sodium periodate → 2-[[(4S,5S)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester

HRID 1354481Notes

Reaction equation

HRID 1354481 reaction equation
[OH:1][CH:2]([C@H:6]1[O:10][C:9]([CH3:12])([CH3:11])[O:8][C@H:7]1[CH2:13][O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])C(O)C.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[CH:2]([C@H:6]1[O:10][C:9]([CH3:12])([CH3:11])[O:8][C@H:7]1[CH2:13][O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:1]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 865887692-[[(4S,5R)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester

Product 1

HCID 865887702-[[(4S,5S)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl esterYield 75.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 2-[[(4S,5R)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester (20 g, 72 mmol) in acetone (20 mL) was diluted with water (400 mL) and treated with solid sodium periodate (26.13 g, 122 mmol). The reaction was analyzed by TLC and was complete after stirring for 1 hour. The reaction mixture was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried, and concentrated to give 12.6 g of 2-[[(4S,5S)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester, a compound of formula (M), as a slightly yellow viscous oil; 1H NMR (CDCl3) δ 1.38 (s, 3H), 1.57 (s, 3H), 3.75 (m, 2H), 3.7 (s, 3H), 4.08 (m, 2H), 4.42 (m, 1H), 4.54 (m, 1H), 9.64 (d, 1H) ppm.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb85338492404b80845ee96bad100868
Source dataset
uspto-grants-2007_05
Patent number
US07223798B2

Reaction notes

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