Water → HCID 59479065, compound

HRID 1747024Notes

Reaction equation

HRID 1747024 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C1C=CN=CC=1)C.ClCCl.C(Cl)(Cl)Cl>[C:17]([O:9][CH2:8][C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 59479065HCID 59479065, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 958 mg of (6-methylpyridin-3-yl)methanol, 1.3 ml of triethylamine, and 95 mg of DMAP in 40 ml of dichloromethane was added dropwise 1.08 ml of benzoyl chloride, followed by stirring at room temperature. To the reaction solution was added water, followed by carrying out an extraction operation with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 1767 mg of (6-methylpyridin-3-yl)methyl benzoate.

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e2b4a2c1704b4510a5825a4e998bb08f
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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