Ammonia → HCID 58134867, compound

HRID 1396099Notes

Reaction equation

HRID 1396099 reaction equation
C[Si](C)(C)Cl.Br[CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:14]1(=[O:18])[CH2:17][CH2:16][CH2:15]1.N>CCOCC.[Zn]>[OH:18][C:14]1([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 14496CyclobutanoneHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 58134867HCID 58134867, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Trimethylchlorosilane (950 μL, 7.43 mmol) was added by syringe to a suspension of zinc powder (6.65 g, 0.102 mol) in absolute Et2O (170 mL). The mixture was stirred for 15 minutes at room temperature, heated to reflux, the heat source removed, and ethyl 2-bromopropionate (10.1 mL, 77.8 mmol) was added at such a rate that the ether gently boiled. After being heated to reflux for 1 hour, the mixture was stirred for 1 hour at room temperature. A solution of cyclobutanone (5.00 g, 63.2 mmol) in Et2O (10 mL) was added while the temperature of the mixture was maintained at 19-20° C. by intermittent cooling. After stirring for 1 hour at room temperature, the mixture was poured into iced 25% ammonia (400 mL). The aqueous phase was extracted with ether, the combined organic phases were dried over K2CO3, and concentrated. the title compound was given as a colorless oil (12.9 g, 100%). 1H-NMR (400 MHz, CDCl3) δ1.21 (3H, d, J=6.8 Hz), 1.29 (3H, t, J=7.3 Hz), 1.51-1.64 (1H, m), 1.80-1.90 (1H, m), 1.96-2.17 (4H, m), 2.70 (1H, q, J=7.3 Hz), 3.44 (1H, s), 4.18 (2H, qd, J=7.3 and 1.2 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customthe heat source removed
  4. temperatureAfter being heated
  5. temperatureto reflux for 1 hour
  6. stirringthe mixture was stirred for 1 hour at room temperature
  7. temperaturewas maintained at 19-20° C. by intermittent cooling
  8. stirringAfter stirring for 1 hour at room temperature
  9. extractionThe aqueous phase was extracted with ether
  10. dry with materialthe combined organic phases were dried over K2CO3
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ecced11f1d664e70b0ba37ef0908ea59
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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