Benzyl Alcohol → HCID 86679674, compound

HRID 577747Notes

Reaction equation

HRID 577747 reaction equation
CC1([C:7]([OH:9])=O)CC(=C)C1.CC[N:12](CC)CC.[N-]=[N+]=[N-].[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=C[CH:29]=1>CCOC(C)=O>[CH3:31][C:32]1([NH:12][C:7](=[O:9])[O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:33][C:28](=[CH2:29])[CH2:34]1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 8471TriethylamineHCID 33558AzideHCID 206145171-Methyl-3-methylidenecyclobutane-1-carboxylic acid

Product 1

HCID 86679674HCID 86679674, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-methyl-3-methylidenecyclobutanecarboxylic acid (2.60 g, 20.6 mmol) in toluene (30 mL) was added Et3N (4.30 mL, 30.9 mmol), followed by diphenylphosphoic azide (6.10 mL, 28.3 mmol). The mixture was stirred at rt for 45 min, then benzyl alcohol (7.60 mL, 73.4 mmol) was added, and the mixture was heated at 80° C. overnight. The mixture was then cooled to rt, diluted with EtOAc (30 mL), washed with sat. NH4Cl (three×40 mL), brine (40 mL), dried over Na2SO4 and concentrated to give the crude title compound as a pale yellow oil. m/z (APCI+) for C14H17NO2232.20 (M+H)+.

Workup

  1. temperaturethe mixture was heated at 80° C. overnight
  2. temperatureThe mixture was then cooled to rt
  3. washwashed with sat. NH4Cl (three×40 mL), brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af5b6f89140b4f649f0a4f8c33f96687
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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