Hydrochloric Acid → HCID 59028462, compound

HRID 2369830Notes

Reaction equation

HRID 2369830 reaction equation
C([O:4][C:5]1[CH:16]=[CH:15][C:8]2[CH:9]=[C:10]([C:12](=[O:14])[CH3:13])[O:11][C:7]=2[CH:6]=1)(=O)C.C(NC(C)C)(C)C.[Li].[C:25](Cl)(=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>O1CCCC1.C(OCC)(=O)C>[OH:4][C:5]1[CH:16]=[CH:15][C:8]2[CH:9]=[C:10]([C:12](=[O:14])[CH2:13][C:25](=[O:34])/[CH:26]=[CH:27]/[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:11][C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 660233-Phenylprop-2-enoyl chlorideHCID 126480921-[6-(Acetyloxy)-2-benzofuranyl]ethanoneHCID 45051747Lithium diisopropylamine

Product 1

HCID 59028462HCID 59028462, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude 2-acetyl-1-benzofuran-6-yl acetate (0.23 g) in tetrahydrofuran (5 mL) at −78° C. was added lithium diisopropylamine (2.0 N solution in THF, 1.63 mL, 3.25 mmol). The mixture was stirred at the same temperature for 20 min prior to the addition of cinnamoyl chloride (0.22 g, 1.3 mmol). The reaction was warmed slowly to room temperature and stirred overnight. The reaction was treated with 1.0 N aqueous hydrochloric acid solution (10 mL) at 0° C. and diluted with ethyl acetate (250 mL). The organic layer was washed with 2N aqueous hydrochloric acid (100 mL), saturated aqueous sodium chloride (60 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude product. Purification on silica (gradient 8:2 to 6:4, hexanes/ethyl acetate) afforded the product (0.12 g, 30% yield) as a yellow solid: MS (EI) for C19H14O4: 307 (MH+).

Workup

  1. stirringstirred overnight
  2. washThe organic layer was washed with 2N aqueous hydrochloric acid (100 mL), saturated aqueous sodium chloride (60 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford crude product
  7. customPurification on silica (gradient 8:2 to 6:4, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-1555ecb10c3c42c3b9389ac35c9619a2
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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