Tetrahydrofuran → HCID 66662076, compound

HRID 2275667Notes

Reaction equation

HRID 2275667 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]#[N:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[O:14]1CCCC1.Cl[N:20]1C(=O)C[CH2:22][C:21]1=O.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:22][C:21]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3([C:12]#[N:13])[CH2:10][CH2:11]3)=[CH:5][CH:4]=2)=[CH:2][O:14][N:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 866022871-(4-Ethynylphenyl)cyclopropane-1-carbonitrile

Product 1

HCID 66662076HCID 66662076, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(4-ethynylphenyl)cyclopropanecarbonitrile (200 mg, 0.001 mol) acetaldoxime (71 mg, 0.0012 mol) in tetrahydrofuran (5.0 mL, 0.062 mol) was added N-chlorosuccinimide (160 mg, 0.0012 mol) in portions with stirring. After the addition was complete, triethylamine (170 μL, 0.0012 mol) was added. The mixture was stirred at rt for 2 days. The reaction mixture was diluted with ethyl acetate and washed with water and brine successively, dried over MgSO4 and filtered. The filtrate was concentrated to afford the desired product in quantitative yield.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred at rt for 2 days
  3. washwashed with water and brine successively
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bca6e7e126314f2f9238b36a5d928933
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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