Acetic Anhydride → HCID 19828478, compound

HRID 1494525Notes

Reaction equation

HRID 1494525 reaction equation
[CH3:1][C:2]1([CH3:22])[O:7][CH2:6][C:5]2[C:8]([CH:13]([OH:21])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][N:10]=[C:11]([CH3:12])[C:4]=2[O:3]1.[C:23](OC(=O)C)(=[O:25])[CH3:24].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:22])[O:7][CH2:6][C:5]2[C:8]([CH:13]([O:21][C:23](=[O:25])[CH3:24])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][N:10]=[C:11]([CH3:12])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 11529834(+/-)-4-Chlorophenyl-5-[(3,4-isopropylidine)-2-methylpyridine]methanol

Product 1

HCID 19828478HCID 19828478, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

210 mg (0.66 mmoles) of (+)-2,2,8-trimethyl-5-(4-chloro-α-hydroxybenzyl)-pyrido-[4,3-e]-1,3-dioxane are poured into a 2 ml vial and dissolved in 500 μl of pyridine and 110 μl of acetic anhydride (1.16 mmole). The reaction mixture is stirred for 18 hours, then poured into 30 ml of saturated NaHCO3. The mixture is allowed to stir at room temperature for 1 hour, then extracted with 3×30 ml of CH2Cl2. The combined CH2Cl2 layers are washed with 3×20 ml of 2N HCl. The organic phase is dried over Na2SO4, filtered and the filtrate is evaporated to dryness. 24 g are obtained as a white solid with a yield of 100%.

Workup

  1. stirringto stir at room temperature for 1 hour
  2. extractionextracted with 3×30 ml of CH2Cl2
  3. washThe combined CH2Cl2 layers are washed with 3×20 ml of 2N HCl
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated to dryness
  7. custom24 g are obtained as a white solid with a yield of 100%

Sources & evidence

ORD record
ord-b873f21db5254fceb310d1cb3d3da07a
Source dataset
uspto-grants-1991_06
Patent number
US05026855

Reaction notes

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