Sodium Hydroxide → HCID 86727076, compound

HRID 1502028Notes

Reaction equation

HRID 1502028 reaction equation
[CH:1]([C:3]1[C:4]([CH3:10])=[C:5]([C:8]#[N:9])[S:6][CH:7]=1)=[CH2:2].C1C(=O)N(Br)C(=[O:14])C1.[OH-].[Na+]>C(O)(C)(C)C.O>[CH3:10][C:4]1[C:3]([CH:1]2[CH2:2][O:14]2)=[CH:7][S:6][C:5]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 86727075HCID 86727075, compound

Product 1

HCID 86727076HCID 86727076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 4-ethenyl-3-methylthiophene-2-carbonitrile (1.70 g, 11.4 mmol) in 30 mL of t-Bu-OH and 60 mL of water was added NBS (2.40 g, 13.7 mmol) portionwise. The mixture was stirred at 90° C. for 1 hour then cooled down to 10° C. Then a solution of NaOH (0.7 g in 10 mL of water, 17.5 mmol) was added dropwise and stirred for 15 minutes. The reaction mixture was extracted with EtOAc twice and concentrated. The residue was purified by silica column chromatography (petrol ether: EtOAc=20:1) to afford 3-methyl-4-(oxiran-2-yl)thiophene-2-carbonitrile.

Workup

  1. temperaturethen cooled down to 10° C
  2. stirringstirred for 15 minutes
  3. extractionThe reaction mixture was extracted with EtOAc twice
  4. concentrationconcentrated
  5. customThe residue was purified by silica column chromatography (petrol ether: EtOAc=20:1)

Sources & evidence

ORD record
ord-dbff7eff8df543308352e265bce7b8e6
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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