Acetic Anhydride → 1-Methyl-1-(3-pyridyl)-6-isochromanol acetate

HRID 259119Notes

Reaction equation

HRID 259119 reaction equation
[CH3:1][C:2]1([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][O:3]1.C(=O)(O)[O-].[Na+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([CH3:1])([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[O:3][CH2:4][CH2:5]2)(=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 20523919HCID 20523919, compound

Product 1

HCID 541923791-Methyl-1-(3-pyridyl)-6-isochromanol acetate

Procedure

A mixture of 1-methyl-1-(3-pyridyl)-6-isochromanol (5.0 g), described in Example 22, and acetic anhydride (50 ml) is heated on the steam bath for 4 hr. The mixture is poured upon ice, left at room temperature for 1 hr, rendered basic with sodium bicarbonate and then extracted with chloroform. The extracts are washed with brine, dried, evaporated, and the residue is crystallized from isopropanol to give the title compound, m.p. 113°-115° C.

Workup

  1. temperatureis heated on the steam bath for 4 hr
  2. additionThe mixture is poured upon ice
  3. extractionextracted with chloroform
  4. washThe extracts are washed with brine
  5. customdried
  6. customevaporated
  7. customthe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-b866fa8adcd345daa153eba2879a6034
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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