Trifluoroacetic acid → HCID 23260547, compound

HRID 2058148Notes

Reaction equation

HRID 2058148 reaction equation
[OH:1][CH:2]1[CH2:19][CH2:18][C:17]2[C:4](=[C:5]([OH:24])[C:6]3[C:7](=[O:23])[C:8]4[C:13]([C:14](=[O:21])[C:15]=3[C:16]=2[OH:20])=[C:12]([OH:22])[CH:11]=[CH:10][CH:9]=4)[CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O>CS(C)=O>[OH:20][C:16]1[C:15]2[C:14](=[O:21])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:22])[C:7](=[O:23])[C:6]=2[C:5]([OH:24])=[C:4]2[C:17]=1[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 20296116HCID 20296116, compound

Product 1

HCID 23260547HCID 23260547, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The alcohol of Example 20 (35 mg) was treated with 130 mg of dicyclohexylcarbodiimide and 0.4 ml of trifluoroacetic acid and 3 ml of dimethyl sulfoxide for 3 hours and then extracted several times with benzene. Evaporation of the benzene layers produced brown-red 5,7,12-trihydroxy-1,2,3,4,6,11-hexahydro-2,6,11-trioxonaphthacene (formula 18), m.p. above 300° C., infrared maximum 1730 cm-1).

Workup

  1. extractionextracted several times with benzene
  2. customEvaporation of the benzene layers

Sources & evidence

ORD record
ord-3541c646ebf44c07966c390bb45fdf1c
Source dataset
uspto-grants-1980_07
Patent number
US04215062

Reaction notes

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