Trimethylsilyldiazomethane → HCID 67080255, compound

HRID 510600Notes

Reaction equation

HRID 510600 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-eeba561284dc49bbad8ab058947ce57e
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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