Hydrochloric Acid → HCID 19384463, compound

HRID 2399804Notes

Reaction equation

HRID 2399804 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([O:10][C:11]2[CH:12]=[CH:13][CH:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=3)[C:15]3[C:19]=2[N:18]=[C:17]2[CH2:20][CH2:21][CH2:22][CH2:23][C:16]=32)=[CH:8][CH:9]=1)=[O:4].O[Li].O.Cl>O1CCCC1.O>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:14]2[C:15]3=[C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:17]4=[N:18][C:19]3=[C:11]([O:10][C:7]3[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)[CH:12]=[CH:13]2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67785061HCID 67785061, compound

Product 1

HCID 19384463HCID 19384463, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the methyl ester (0.9 g) from Example 114 in 10 mL of tetrahydrofuran was treated with a solution of 0.8 g of LiOH.H2O in 10 mL water. The reaction mixture was stirred at room temperature for 28 h, diluted with water, acidified with 2N-HCl and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 5-[[1,2,3,4-tetrahydro-9-(4-bromophenyl)methyl-9H-dibenzo[b,d]pyrrol-6-yl]oxy]-2-furancarboxylic acid (0.35 g; 40.0%) as a white solid after repeated crystallizations from ethyl acetate, mp 155.5°-157.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f05ee6d8683f42cfbe25e7a42125792a
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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