Triethylamine → HCID 21086146, compound

HRID 348940Notes

Reaction equation

HRID 348940 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[CH2:14]([N:16]([CH2:19]C)CC)[CH3:15].CS(Cl)(=O)=[O:23]>C(Cl)Cl>[OH:23][CH2:15][CH2:14][N:16]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

Product 1

HCID 21086146HCID 21086146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.1 mmol) in methylene chloride (2.2 mL) is added triethylamine (0.304 mL, 2.2 mmol) followed by methanesulfonyl chloride (0.116 mL, 1.5 mmol). The reaction mixture is stirred for 15 min and filtered. 2-Methoxy-N-methyleneamine (0.354 mL, 3.3 mmol) is added to the filtrate and stirred at room temperature for 5 h. The reaction mixture is diluted with methylene chloride (10 mL), washed with 1 N hydrochloric acid, and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (50% ethyl acetate/hexanes) provides the title compound. ESI MS m/z 238 [M+H]+.

Workup

  1. filtrationfiltered
  2. stirringstirred at room temperature for 5 h
  3. washwashed with 1 N hydrochloric acid, and saturated sodium bicarbonate
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0db21b25a3af4b44a754dfe43454b092
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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