2,2-Dimethoxypropane → HCID 11645721, compound

HRID 888169Notes

Reaction equation

HRID 888169 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]([C@H:17]([OH:21])[C:18]([OH:20])=[O:19])[C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)[CH3:2].CO[C:24](OC)([CH3:26])[CH3:25]>CC(C)=O.[Cu](Cl)Cl>[CH3:25][C:24]1([CH3:26])[O:21][C@@H:17]([C@@H:13]([CH2:12][CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=2)[C:14]([OH:16])=[O:15])[C:18](=[O:20])[O:19]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 59696742HCID 59696742, compound

Product 1

HCID 11645721HCID 11645721, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R,3S)-2-[3-(4-ethoxyphenyl)propyl]-3-hydroxybutanedioic acid (3.06 g; 10.33 mmol; 1.0 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (1.8 g; 17.6 mmol; 1.7 eq.) and copper(II) chloride (135 mg; 1.03 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 14 h at RT. The reaction mixture was evaporated and the residue taken up in Et2O. Filtration on a pad of celite gave the title product as a greenish oil used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 7.05 (d, J=8.6 Hz, 2H), 6.80 (d, J=8.6 Hz, 2H), 4.48 d (J=5.0 Hz, 1H), 3.98 (q, J=7.0 Hz, 2H), 3.10-2.81 (m, 1H), 2.74-2.41 (m, 3H), 220-1.15 (m, 4H), 1.61 (s, 3H), 1.50 (s, 3H), 1.35 (t, J=7.0 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. filtrationFiltration on a pad of celite

Sources & evidence

ORD record
ord-a3ed32543bc54ff3ab4bf8995a0d006c
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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