Benzyl Alcohol → HCID 14919389, compound

HRID 1396315Notes

Reaction equation

HRID 1396315 reaction equation
[CH3:1][CH:2]([CH:6]=[CH2:7])[C:3]([OH:5])=[O:4].[C:8]1([CH2:14]O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=NC1CCCCC1)=NC1CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][CH:2]([CH:6]=[CH2:7])[C:3]([O:5][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 1430882-Methylbut-3-enoic acid

Product 1

HCID 14919389HCID 14919389, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylbut-3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N,N′-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the resulting mixture was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE® to remove the solids and the filtrate was collected and concentrated. The filtrate was then concentrated and subjected to silica gel chromatography to yield the desired product as colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. customto remove the solids
  3. customthe filtrate was collected
  4. concentrationconcentrated
  5. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-9ae8d3de3dbe41f9a66921f89014c074
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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