Hexane → HCID 42965579, compound

HRID 1670670Notes

Reaction equation

HRID 1670670 reaction equation
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[C:14]1([C:20]23[CH2:29][CH:24]4[CH2:25][CH:26]([CH2:28][C:22]([C:30]([OH:32])=[O:31])([CH2:23]4)[CH2:21]2)[CH2:27]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.CO>[C:14]1([C:20]23[CH2:29][CH:24]4[CH2:25][CH:26]([CH2:28][C:22]([C:30]([O:32][CH3:8])=[O:31])([CH2:23]4)[CH2:21]2)[CH2:27]3)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 377913-Phenyladamantane-1-carboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 42965579HCID 42965579, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane 2M solution in hexane (8.15 mL, 16.31 mmol) was added dropwise to a stirred solution of 3-phenyl-1-adamantanecarboxylic acid (2.09 g, 8.15 mmol, CAS 37589-22-3) in toluene (20 mL) and methanol (10 mL) over a period of 2 minutes. The resulting solution was stirred at ambient temperature for 60 minutes. The reaction mixture was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (2.140 g, 97%) as a colourless oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customto afford crude product
  3. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  4. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-7c9e4894737b407782c22f6a05433183
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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