Ammonium Acetate → HCID 18967712, compound

HRID 1490167Notes

Reaction equation

HRID 1490167 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][O:10][C:9]2(O)[CH2:12][CH2:13][CH:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:15][CH:8]2[CH2:7]1)=O)C.C([O-])(=O)C.[NH4+:30]>CO>[OH:10][CH2:11][CH:6]1[CH2:7][C:8]2[CH2:15][CH:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:13][CH2:12][C:9]=2[NH:30][C:4]1=[O:3]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 18967733HCID 18967733, compound

Product 1

HCID 18967712HCID 18967712, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4,4a,5,6,7,8,8a-Octahydro-3-ethoxycarbonyl-8a-hydroxy-6-(4-methoxyphenyl)methyl-2H-benzo[b]pyran (21 g) in methanol (100 ml) was heated under reflux with ammonium acetate (40 g) for 18 hours. The mixture was evaporated to dryness and the residue partitioned between water and chloroform. The chloroform extract was dried (Na2SO4), treated with charcoal and evaporated to give an oil. This was crystallised from ethylacetate to give the title compound mp 165°-168° C.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between water and chloroform
  3. extractionThe chloroform extract
  4. dry with materialwas dried (Na2SO4)
  5. additiontreated with charcoal
  6. customevaporated
  7. customto give an oil
  8. customThis was crystallised from ethylacetate

Sources & evidence

ORD record
ord-9af750a7a2d04f34af576ca3b51b109b
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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