Trimethylsilyldiazomethane → HCID 58216816, compound

HRID 467981Notes

Reaction equation

HRID 467981 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]([CH2:8][CH3:9])[CH2:4][C:5]([OH:7])=[O:6].[CH3:12][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[CH3:12][O:6][C:5](=[O:7])[CH2:4][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 144070623-(Trifluoromethyl)pentanoic acid

Product 1

HCID 58216816HCID 58216816, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 1D (250 mg, 1.47 mmol) in dichloromethane (10 mL) and methanol (0.25 mL), under nitrogen atmosphere, trimethylsilyldiazomethane (2.0 M solution in diethyl ether) (2.1 mL, 4.19 mmol) was added drop wise at 0° C. The reaction mixture was stirred keeping the temperature below 5° C. for 1 h. The solvent was removed (40° C., 25 bar) yielding 250 mg (75.4%) of a yellow oil that was used in the next step without further purification.

Workup

  1. customthe temperature below 5° C.
  2. customfor 1 h
  3. customThe solvent was removed (40° C., 25 bar)

Sources & evidence

ORD record
ord-a0f7fe8552204be781ea4b09847154ee
Source dataset
uspto-grants-2014_01
Patent number
US08623901B2

Reaction notes

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