Hydrochloric Acid → HCID 22614989, compound

HRID 843146Notes

Reaction equation

HRID 843146 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][Br:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.O[Li].O.O.Cl>C1COCC1.CO>[Br:20][CH2:19][CH2:18][CH2:17][O:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 54377087Ethyl 4-(3-bromopropoxy)-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 22614989HCID 22614989, compoundYield 112.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (27.3 g), the compound in Example 5-a, was dissolved in THF (546 ml) and cooled at 0° C. To the solution were added LiOH.H2O (6.72 g), water (410 ml) and MeOH (135 ml). The mixture was stirred at room temperature for seven hours. To the reaction mixture was added 1N-HCl (133 ml). After evaporating the organic solvent, the mixture was mixed with ethyl acetate (1,400 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to give colorless needles. The colorless needles were washed with ethyl acetate-hexane (2:8) to obtain pure 4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid (28.3 g). FAB-MS: m/z 312 (M+); 1H-NMR (CDCl3): δ 2.43 (2H, quintet, J=6.5 Hz), 2.78 (3H, s), 3.66 (2H, t, J=6.5 Hz), 4.25 (2H, t, J=6.5 Hz), 6.67 (1H, d, J=8 Hz), 7.17 (1H, d, J=8 Hz), 7.38 (1H, t, J=8 Hz).

Workup

  1. customAfter evaporating the organic solvent
  2. additionthe mixture was mixed with ethyl acetate (1,400 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give colorless needles
  6. washThe colorless needles were washed with ethyl acetate-hexane (2:8)

Sources & evidence

ORD record
ord-afd9c1658dfa4f39bddc6cc549b8aee6
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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