2,2-Dimethoxypropane → HCID 67087136, compound

HRID 2365574Notes

Reaction equation

HRID 2365574 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C@@H:17]([OH:20])[CH2:18][OH:19])[CH:11]=2)[CH:6]=1)=[O:4].CO[C:23](OC)([CH3:25])[CH3:24].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C@@H:17]3[CH2:18][O:19][C:23]([CH3:25])([CH3:24])[O:20]3)[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67087007HCID 67087007, compound

Product 1

HCID 67087136HCID 67087136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-((S)-2,3-dihydroxy-propoxy)-naphthalene-2-carboxylic acid methyl ester (0.9 g, 3.26 mmol) in anhydrous DMF (10 ml) is added 2,2-dimethoxypropane (2.0 ml, 16.3 mmol) and pyridinium p-toluenesulfonate (0.08 g, 0.32 mmol) and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated in vacuo and the residue is dissolved in EtOAc. The EtOAc layer is washed with 10% NaHCO3, water, and brine, dried over anhydrous Na2SO4 and the solvent is evaporated in vacuo to obtain 6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester as solid; 1H NMR (DMSO-d6): 1.32 (3H, s), 1.37 (3H, s), 3.78-3.82 (1H, m), 3.88 (3H, s), 4.11-4.20 (3H, m), 4.45-4.50 (1H, m), 7.26 (1H, dd, J=9.0, 2.0 Hz), 7.45 (1H, d, J=2.0 Hz), 7.88 (1H, d, J=9.0 Hz), 7.93 (1H, d, J=9.0 Hz), 8.04 (1H, d, J=9.0 Hz), 8.55 (1H, s).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in EtOAc
  3. washThe EtOAc layer is washed with 10% NaHCO3, water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-50cc98c934f646c5b950a47cb985de0a
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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