Triethylamine → HCID 22033391, compound

HRID 1792321Notes

Reaction equation

HRID 1792321 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][CH2:13][C:12]1([CH3:29])[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].[NH4+].[Cl-]>C(Cl)Cl>[CH3:37][S:38]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][CH2:13][C:12]1([CH3:29])[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 22033419HCID 22033419, compound

Product 1

HCID 22033391HCID 22033391, compoundYield 380.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(9-hydroxynonyl)-7-methoxy-3-methyl-3-(4-pyridyl)chroman (108 mg, 0.272 mmol) in methylene chloride (2 mL) were added under ice-cooling triethylamine (0.057 mL, 0.41 mmol) and methanesulfonyl chloride (0.032 ml, 0.41 mmol), which was then stirred for 30 minutes. After the reaction was completed, saturated aqueous NH4Cl solution was added, the resulting mixture was then extracted with methylene chloride and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4-(9-methanesulfonyloxynonyl)-7-methoxy-3-methyl-3-(4-pyridyl)chroman (492 mg, yield 38%).

Workup

  1. extractionthe resulting mixture was then extracted with methylene chloride
  2. washwashed with saturated saline solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b3eb975fd19746b1b04fffaf5e0b855e
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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