HCID 66644024, compound → HCID 77231262, compound

HRID 2173171Notes

Reaction equation

HRID 2173171 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[CH3:16][C:17](N=C([O-])N(C(C)C)C(C)C)([CH3:19])[CH3:18]>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([O:15][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 66644024HCID 66644024, compoundHCID 86693003HCID 86693003, compound

Product 1

HCID 77231262HCID 77231262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetic acid (100 mg, 0.48 mmol) in anhydrous DCM (10 mL) was added 1,1-dimethylethyl-N,N-bis(1-methylethyl)imidocarbamate (485 mg, 2.50 mmol) dropwise at 0° C. under N2. Then the mixture was stirred at r.t. over night. The mixture was filtered and the filtrate was washed with 2N HCl and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to give 1,1-dimethylethyl (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 6 ppm 7.70 (d, J=7.8 Hz, 1H), 7.38 (d, J=7.0 Hz, 1H), 5.25 (s, 2H), 3.67 (s, 3H), 2.27 (s, 3H), 1.44 (s, 9H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with 2N HCl and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-90db1497cc8e433f95ef11fa4715f70f
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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