Methanol → HCID 15390840, compound

HRID 619777Notes

Reaction equation

HRID 619777 reaction equation
[OH-].[K+].C(N(CC)CC)C.[CH3:10][O:11][C:12]1[C:13]([O:29]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:14][C:15]2[CH2:24][CH2:23][C:22](=[O:25])[C:21]3[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[C:26]=1[O:27][CH3:28].CO>O.C(O)(=O)C>[CH3:10][O:11][C:12]1[C:13]([OH:29])=[CH:14][C:15]2[CH2:24][CH2:23][C:22](=[O:25])[C:21]3[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[C:26]=1[O:27][CH3:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 18421092HCID 18421092, compound

Product 1

HCID 15390840HCID 15390840, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4.5 g of potassium hydroxide, then 10 ml of triethylamine were added to a suspension of 10 g of 9,10-dimethoxy 8-(((4-methylphenyl)sulfonyl)oxy) 2,3,5,6-tetrahydro-benz[e]-azulen-4(1H)-one of Stage B of Example 3 and 100 ml of methanol. The reaction medium was heated for one hour at reflux, acidified by the addition of 20 ml of acetic acid and then 20 ml of water were added. Extraction was carried out with dichloromethane and the extracts were washed with water. The solvent was evaporated at 40° C. under reduced pressure to obtain 5.7 g of the expected product which was used as is for the following stage.

Workup

  1. temperatureThe reaction medium was heated for one hour
  2. temperatureat reflux
  3. extractionExtraction
  4. washthe extracts were washed with water
  5. customThe solvent was evaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-9595c13967b34f96aee32c40c964a320
Source dataset
uspto-grants-1999_09
Patent number
US05959146

Reaction notes

Loading…