Dimethyl Sulfoxide → HCID 54571041, compound

HRID 1250101Notes

Reaction equation

HRID 1250101 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:28])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[C:20]=1[CH3:27])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[C:11]([O:15][C:16](=[O:28])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[C:20]=1[CH3:27])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11817603HCID 11817603, compound

Product 1

HCID 54571041HCID 54571041, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.46 mL, 5.25 mmol) was added dropwise to a solution of dimethyl sulfoxide (0.88 mL, 12.50 mmol) dissolved in dichloromethane (40 mL). The mixture was cooled to −78° C. and allowed to stir for 1 hour. A solution of (3-hydroxymethyl-2-methylphenoxy)acetic acid tert-butyl ester (1.26, 5.00 mmol) in dichloromethane was cannulated into the reaction mixture and allowed to stir at −78° C. for an additional hour. Triethylamine (3.49 mL, 25 mmol) was added. The reaction mixture was allowed to warm to room temperature, poured into water, and the layers were separated. The aqueous layer was extracted twice with dichloromethane. The combined organic extracts were washed with 2N hydrochloric acid and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography, eluting with hexane/acetone, gave (3-formyl-2-methylphenoxy)acetic acid tert-butyl ester as a slightly yellow crystalline solid (1.07 g, 85.9%).

Workup

  1. stirringto stir at −78° C. for an additional hour
  2. temperatureto warm to room temperature
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with dichloromethane
  5. washThe combined organic extracts were washed with 2N hydrochloric acid and saturated sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography
  9. washeluting with hexane/acetone

Sources & evidence

ORD record
ord-e3310b599cc044688036e9c3bc24c263
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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