Triethylamine → Cyanomethyl 2-(allyloxy)acetate

HRID 1482377Notes

Reaction equation

HRID 1482377 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([OH:8])=[O:7])[CH:2]=[CH2:3].Br[CH2:10][C:11]#[N:12].C(N(CC)CC)C>ClCCl>[CH2:1]([O:4][CH2:5][C:6]([O:8][CH2:10][C:11]#[N:12])=[O:7])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 109970062-(Prop-2-en-1-yloxy)acetic acid

Product 1

HCID 91618380Cyanomethyl 2-(allyloxy)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Allyloxy)acetic acid (0.500 g, 4.31 mmol) was dissolved in dichloromethane (20 ml), and 2-bromoacetonitrile (2.06 g, 17.18 mmol) and triethylamine (0.87 g, 8.61 mmol) were slowly added at room temperature. After stirring at room temperature for 3 hours, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford cyanomethyl 2-(allyloxy)acetate (0.40 g, 60%).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-15b1999e72884665812c6f34cdce6047
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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