Sodium Iodide → HCID 15907471, compound

HRID 921710Notes

Reaction equation

HRID 921710 reaction equation
[OH:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C.[I-].[Na+]>CCOC(C)=O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 699934-Methyloxybenzyl chlorideHCID 81531DiisopropylethylamineHCID 94386methyl (S)-lactate

Product 1

HCID 15907471HCID 15907471, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (S)-methyl 2-hydroxypropanoate (1.5 g, 14.41 mmol), 1-(chloromethyl)-4-methoxybenzene (3.38 g, 21.61 mmol), DIPEA (4.03 ml, 23.05 mmol) and sodium iodide (0.150 g, 1.001 mmol) was heated to 150° C. for 2 h. Reaction mixture then was cooled to room temperature diluted with EtOAc (100 mL) and washed with saturated NaHCO3 solution (2×50 mL) and brine. Combined organic extracts were dried over anhydrous Na2SO4 and concentrated. The crude mixture was purified by flash chromatography on silica gel using an ISCO system (eluted with 9:1 Hexanes and EtOAc) to give (S)-methyl 2-((4-methoxybenzyl)oxy)propanoate (2 g) as a gummy liquid.

Workup

  1. customReaction mixture
  2. temperaturethen was cooled to room temperature
  3. washwashed with saturated NaHCO3 solution (2×50 mL) and brine
  4. dry with materialCombined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude mixture was purified by flash chromatography on silica gel using
  7. washan ISCO system (eluted with 9:1 Hexanes and EtOAc)

Sources & evidence

ORD record
ord-dc858179a1e94063b73414c8e2181075
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…