Hydrochloric Acid → HCID 12741941, compound

HRID 1579642Notes

Reaction equation

HRID 1579642 reaction equation
[CH3:1][C:2]1[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]2[CH2:7][C:6](Br)([CH2:17][CH2:18][CH3:19])[C:5](=[O:21])[C:4]=2[C:3]=1[CH3:22].O.Cl>CS(C)=O>[CH3:1][C:2]1[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]2[CH:7]=[C:6]([CH2:17][CH2:18][CH3:19])[C:5](=[O:21])[C:4]=2[C:3]=1[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 12741940HCID 12741940, compound

Product 1

HCID 12741941HCID 12741941, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4,5-dimethyl-6-oxo-7-bromo-7-propyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid (0.70 g., 0.0019 mole) and 1,5-diazabicyclo-[4.3.0]-5-one (0.5 ml.) in dimethylsulfoxide (5 ml.) is stirred at 25°C. in an inert atomsphere for 1 1/2 hours, treated with water (15 ml.) acidified with hydrochloric acid, extracted with ether washed with water and dried over magnesium sulfate. The ether is evaporated at reduced pressure and the crude product crystallized from nitromethane (10 ml.) affording 4,5-dimethyl-6-oxo-7-propyl-1,2-dihydro-6H-indeno[5,4-b]furan-2-carboxylic acid as a red solid which melts at 212°C.

Workup

  1. extractionextracted with ether
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe ether is evaporated at reduced pressure
  5. customthe crude product crystallized from nitromethane (10 ml.)

Sources & evidence

ORD record
ord-3592023f061449a9a86c5cb35a5ae04b
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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