Hydrochloric Acid → HCID 18505286, compound

HRID 1357287Notes

Reaction equation

HRID 1357287 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([OH:13])=[O:12].C([N-]C(C)C)(C)C.[Li+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C1COCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[CH2:1]([C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([OH:13])=[O:12])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 6005913-Methyl-1-benzofuran-2-carboxylic acidHCID 2724682Lithium diisopropylamide

Product 1

HCID 18505286HCID 18505286, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-10 °C

Procedure

3-Methyl-benzofuran-2-carboxylic acid (9.99 g, 56.7 mmol) in 150 mL of anhydrous THF was added under nitrogen dropwise to a solution of lithium diisopropylamide (60 mL of a 2.0 M solution in heptane/THF/ethylbenzene; 120 mmol) in 350 mL of anhydrous THF at −10° C. After the addition was complete the reaction was stirred at −10° C. for approximately 10 minutes. Benzyl bromide (13.5 mL, 113 mmol) was then added dropwise to the reaction. After the addition the reaction was allowed to warm to room temperature and then stirred at room temperature for 2 h. The reaction was acidified by the addition of 1 N HCl and then concentrated under reduced pressure to remove the THF. The residue was partitioned between 1 N HCl and methylene chloride. The aqueous layer was separated and extracted two times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure. The residue was recrystallized from ethyl acetate to give 3-phenethyl-benzofuran-2-carboxylic acid (1.62 g, 11%) as a white solid, mp 169-172° C.

Workup

  1. customat −10° C
  2. additionAfter the addition
  3. additionAfter the addition the reaction
  4. temperatureto warm to room temperature
  5. stirringstirred at room temperature for 2 h
  6. concentrationconcentrated under reduced pressure
  7. customto remove the THF
  8. customThe residue was partitioned between 1 N HCl and methylene chloride
  9. customThe aqueous layer was separated
  10. extractionextracted two times with methylene chloride
  11. dry with materialThe combined extracts were dried (MgSO4)
  12. customthe solvent removed under reduced pressure
  13. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fbbf9ffe2f894bc78e40f1827b9ea5e7
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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