Hydrochloric Acid → 1-(2,3-Dihydro-1-benzofuran-7-yl)ethan-1-one

HRID 1940596Notes

Reaction equation

HRID 1940596 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:13][Li].Cl>C(OCC)C>[C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)(=[O:12])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 106070731-(2,3-Dihydro-1-benzofuran-7-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cooled suspension of 2,3-dihydrobenzofuran-7-carboxylic acid (D1) (2 g) in dry diethyl ether (100 ml) was added dropwise under argon, methyllithium (16.2 ml of a 1.5M solution in diethyl ether). The mixture was stirred at room temperature for 18 h, added to 5N hydrochloric acid (50 ml) and extracted into ethyl acetate. The organic phase was washed with potassium carbonate, then water and dried (Na2SO4). The solvent was evaporated under reduced pressure to leave the title compound as a plate lemon solid (1.5 g, 76%)

Workup

  1. additionwas added dropwise under argon
  2. extractionextracted into ethyl acetate
  3. washThe organic phase was washed with potassium carbonate
  4. dry with materialwater and dried (Na2SO4)
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68ff1040be2647289c7f4d896aa4538a
Source dataset
uspto-grants-1997_12
Patent number
US05700818

Reaction notes

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