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

HRID 27773Notes

Reaction equation

HRID 27773 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-3cbeb95033314d238b40aa7ba9df6b02
Source dataset
uspto-grants-1980_09
Patent number
US04223151

Reaction notes

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