Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 10885179, compound

HRID 884376Notes

Reaction equation

HRID 884376 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][CH:9]1[OH:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33]C1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:11][CH2:10][CH:9]1[O:32][CH3:33])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 44556602HCID 44556602, compound

Product 1

HCID 10885179HCID 10885179, compoundYield 1,585%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.92 g of 204 (6.41 mmol) in 10 ml of anhydrous MeOH was added with 100 mg of PPTS (0.40 mmol, 6.2 mole %) and stirred at RT overnight. After checking completion of the reaction by means of TLC (EE/CH 1:7), the solution was concentrated, the remaining residue taken up in 25 ml of ethyl acetate and filtered over a small amount of silica gel. The filtrate was concentrated and further purified using silica gel column chromatography (EE/CH 1:7), thereby obtaining 2.98 g of 59 (6.34 mmol, 99%) as a colorless oil.

Workup

  1. customcompletion of the reaction by means of TLC (EE/CH 1:7)
  2. concentrationthe solution was concentrated
  3. filtrationfiltered over a small amount of silica gel
  4. concentrationThe filtrate was concentrated
  5. customfurther purified

Sources & evidence

ORD record
ord-a3f4d3c1ad8e46178e095718f6387307
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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