2,2-Dimethoxypropane → HCID 58487996, compound

HRID 888218Notes

Reaction equation

HRID 888218 reaction equation
[CH:1]1([CH2:6][C@H:7]([C@H:11]([OH:15])[C:12]([OH:14])=[O:13])[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO[C:18](OC)([CH3:20])[CH3:19]>CC(C)=O.[Cu](Cl)Cl>[CH:1]1([CH2:6][C@H:7]([C@H:11]2[C:12](=[O:14])[O:13][C:18]([CH3:20])([CH3:19])[O:15]2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 58487972HCID 58487972, compound

Product 1

HCID 58487996HCID 58487996, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R,3S)-2-(cyclopentylmethyl)-3-hydroxysuccinic acid (18.97 g, 87.73 mmol; 1.0 eq.) in acetone (300 mL) was added 2,2-dimethoxypropane (21.6 mL, 175.46 mmol, 2.0 eq.) and copper (II) chloride (1.18 g; 8.77 mmol, 0.1 eq.). The resulting reaction mixture was stirred for 16 h at RT. The reaction mixture was evaporated and the residue taken up in CHCl3 (200 mL). Activated charcoal (10 g) was added and the resulting mixture was stirred at RT for 30 minutes. Filtration on a pad of celite gave the title product as yellowish oil. Purification by flash chromatography (Si60; 40-60 microns) eluting with Heptane/MTBE 60/40 gave the title product (16.30 g; 72.5%) as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. additionActivated charcoal (10 g) was added
  4. stirringthe resulting mixture was stirred at RT for 30 minutes
  5. filtrationFiltration on a pad of celite

Sources & evidence

ORD record
ord-c5246ab5590e4890b2e1dd4290b3a1de
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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