Acetic Anhydride → N-(6-benzyloxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

HRID 613439Notes

Reaction equation

HRID 613439 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]([OH:21])[CH:12]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]([O:21][C:28](=[O:30])[CH3:29])[CH:12]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11760985N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Product 1

HCID 11048325N-(6-benzyloxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4.5 g of N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide and 37 ml of acetic anhydride in 74 ml of pyridine was left to stand at RT overnight. The batch was concentrated under reduced pressure and the residue was dissolved in EA, washed successively with dilute hydrochloric acid and saturated sodium bicarbonate solution and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave 4.7 g of N-(6-benzyloxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide, m.p. 124-125° C.

Workup

  1. concentrationThe batch was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in EA
  3. washwashed successively with dilute hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7edc17a160404fb5a066798cd2568d8b
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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