Ethyl Thioglycolate → HCID 89543486, compound

HRID 922779Notes

Reaction equation

HRID 922779 reaction equation
[N+:1](/[CH:4]=[CH:5]/[CH:6]1[CH2:8][CH2:7]1)([O-:3])=[O:2].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][SH:11]>C1COCC1>[CH:6]1([CH:5]([S:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][N+:1]([O-:3])=[O:2])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 12185Ethyl ThioglycolateHCID 14978083Cyclopropane, (2-nitroethenyl)-, (E)-

Product 1

HCID 89543486HCID 89543486, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-(2-Nitrovinyl)cyclopropane (4-11, 750 mg, 6.63 mmol) was taken up in THF (20 mL). To this was added ethyl thioglycolate (0.88 mL, 7.98 mmol) then TEA (1.2 mL, 8.61 mmol) at rt. After stirring overnight the mixture was concentrated. The crude product was subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient) to afford ethyl 2-((1-cyclopropyl-2-nitroethyl)thio)acetate (4-12, 1.46 g, 94%) as a clear oil. 1H NMR (399 MHz, CDCl3): δ 4.73-4.58 (m, 2H); 4.21 (q, J=7.1 Hz, 2H); 3.34 (d, J=6.2 Hz, 2H); 2.93 (dt, J=9.9, 7.2 Hz, 1H); 1.30 (t, J=7.1 Hz, 3H); 1.00-0.90 (m, 1H); 0.69 (dd, J=8.0, 1.6 Hz, 2H); 0.47-0.36 (m, 2H).

Workup

  1. customat rt
  2. concentrationwas concentrated
  3. customwas subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient)

Sources & evidence

ORD record
ord-e7652e7abd3d4b5c8cccbcda51d4bdbf
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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