3-Hydroxybenzaldehyde → HCID 51556787, compound

HRID 1009478Notes

Reaction equation

HRID 1009478 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C@H:11](O)[C:12]([O:14][CH3:15])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+]>C1COCC1>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C@H:11]([CH3:10])[C:12]([O:14][CH3:15])=[O:13])=[O:6]

Participants

7

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 94386methyl (S)-lactateHCID 516892Sodium BicarbonateHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 51556787HCID 51556787, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.50 g of 3-hydroxybenzaldehyde, 2.77 g of methyl L-(−)-lactate, and 6.44 g of triphenylphosphine were dissolved in 25.0 mL of THF, and 22.2 mL of a 2.2 M diethyl azodicarboxylate/toluene solution was added thereto under ice-cooling, followed by stirring at room temperature overnight. To the reaction liquid was added an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3 to 1:1) to obtain 1.67 g of methyl (2R)-2-(3-formylphenoxy)propionate. The obtained methyl (2R)-2-(3-formylphenoxy)propionate was dissolved in 33.3 mL of methanol, and 394 mg of sodium borohydride was added thereto under ice-cooling, followed by stirring for 30 minutes. To the reaction liquid were added ethyl acetate and water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 1.68 g of methyl (2R)-2-[3-(hydroxymethyl)phenoxy]propionate.

Workup

  1. temperatureunder ice-cooling
  2. customTo the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3 to 1:1)

Sources & evidence

ORD record
ord-5891bfd4ca5347258915f0340dbbd523
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

Loading…