Trimethylsilyldiazomethane → HCID 67080255, compound

HRID 1021366Notes

Reaction equation

HRID 1021366 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:18]>C(Cl)Cl.CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]([O:16][CH3:18])=[O:15])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 670803947-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylic acid

Product 1

HCID 67080255HCID 67080255, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylic acid (0.280 g, 1.25 mmol) in CH2Cl2 (5 mL) and MeOH (1 mL) was added TMSCHN2 (0.937 mL, 1.87 mmol) dropwise. After the addition, the reaction was concentrated, loaded onto silica gel, and the product eluted using a gradient of 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes to provide the title compound (0.225 g, 75.6% yield).

Workup

  1. additionAfter the addition
  2. concentrationthe reaction was concentrated
  3. washthe product eluted

Sources & evidence

ORD record
ord-c91d65c1f34a4215b85a6a79e8cf7cf5
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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