4-Toluenesulfonyl chloride → HCID 57022055, compound

HRID 381777Notes

Reaction equation

HRID 381777 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH:12]3[C@H:14]([OH:15])[CH:9]2[CH2:10][CH2:11]3)=[CH:4][CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:15][C@H:14]2[CH:12]3[CH2:11][CH2:10][CH:9]2[C@@:8]([OH:16])([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH2:13]3)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57151856HCID 57151856, compound

Product 1

HCID 57022055HCID 57022055, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 50 mL round-bottomed flask, equipped with a drying tube, was charged with dry pyridine (5 mL), [2R*,7S*]-2-(4-methylphenyl)bicyclo[2.2.1]heptane-2,7-diol (0.8 g, 3.7 mmole, prepared as in Part C above) and p-toluenesulfonyl chloride (0.74 g, 3.88 mmole), and the resultant reaction mixture allowed to stand for 36 hours at ambient temperature. Saturated sodium bicarbonate solution (25 mL) was then added, and the resultant mixture extracted twice with 25 mL aliquots of diethyl ether. The ether extracts were combined, washed with distilled water and dried over anhydrous sodium sulfate, then the ether was removed on a rotary evaporator. The pale yellow solid residue thus produced was purified by flash column chromatography on silica gel using a 1:1 v/v diethyl ether/hexane mixture as eluant, then recrystallized from diethyl ether/pentane to give the desired product as a white crystalline solid, yield 1.0 g, 74% based upon the diol starting material. This product decomposed at 68° C. before melting. The product was characterized as follows:

Workup

  1. customA 50 mL round-bottomed flask, equipped with a drying tube
  2. customthe resultant reaction mixture
  3. extractionthe resultant mixture extracted twice with 25 mL aliquots of diethyl ether
  4. washwashed with distilled water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe ether was removed on a rotary evaporator
  7. customThe pale yellow solid residue thus produced
  8. customwas purified by flash column chromatography on silica gel using a 1:1 v/v diethyl ether/hexane mixture as eluant
  9. customrecrystallized from diethyl ether/pentane

Sources & evidence

ORD record
ord-a8ae29be0c9c4fa99c63862aa5c4c822
Source dataset
uspto-grants-2001_10
Patent number
US06307085B1

Reaction notes

Loading…