4-Toluenesulfonyl chloride → [2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanol

HRID 235978Notes

Reaction equation

HRID 235978 reaction equation
[C:1]1([CH:7]2[N:11]([CH:12]([CH3:21])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH:9]([CH2:22][OH:23])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>N1C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([OH:8])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[C:1]1([CH:7]2[N:11]([CH:12]([CH3:21])[CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:10][CH:9]([CH2:22][OH:23])[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 53876813[2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanol

Product 2

HCID 6101p-Toluenesulfonic acidHCID 53876813[2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanolYield 200%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 95 (7.6 g, 0.025 mol) in pyridine (15 ml) was cooled in an ice bath and p-toluenesulfonyl chloride (4.7 g, 0.025 mol) was added while keeping the internal temperature below 30° C. After stirring for 3 hours at room temperature, a saturated solution of Na2CO3 was added and the mixture extracted with CH2Cl2 (3×). The organic extracts were dried, filtered and concentrated under reduced pressure below 50° C. initially using water aspirator pressure and finally high vacuum to yield the p-toluene sulfonate of 95 (0.025 mol).

Workup

  1. customthe internal temperature below 30° C
  2. extractionthe mixture extracted with CH2Cl2 (3×)
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure below 50° C. initially using water aspirator pressure and finally high vacuum

Sources & evidence

ORD record
ord-6717a113233a4876a31721548cf0354f
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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