HCID 54571041, compound → HCID 54445466, compound

HRID 1250102Notes

Reaction equation

HRID 1250102 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[C:10]=1[CH3:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Mg]Cl>O1CCCC1>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([OH:16])[CH3:19])[C:10]=1[CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 54571041HCID 54571041, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 54445466HCID 54445466, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(3-Formyl-2-methylphenoxy)acetic acid tert-butyl ester (0.94 g, 3.75 mmol) was dissolved in freshly distilled tetrahydrofuran and cooled to −78° C. Methyl magnesium chloride (2.62 mL, 7.88 mmol) was added dropwise and the mixture was allowed to stir at −78° C. for two hours. The mixture was allowed to warm to room temperature, stirred for an additional six hours, then carefully quenched with water, and extracted with ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography, eluting with hexane/acetone, gave [3-(1-hydroxyethyl)-2-methylphenoxy)acetic acid tert-butyl ester as a clear oil (594 mg, 59.5%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional six hours
  3. customcarefully quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography
  8. washeluting with hexane/acetone

Sources & evidence

ORD record
ord-2f0a78f08b5d4368b5ace44c52f71acc
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

Loading…