Hydrochloric Acid → HCID 20087862, compound

HRID 275344Notes

Reaction equation

HRID 275344 reaction equation
[N+:1]([C:4]1[CH2:8][CH2:7][CH2:6][CH:5]=1)([O-:3])=[O:2].I[CH2:10][CH2:11][CH:12]1[O:17][CH2:16][CH2:15][CH2:14][O:13]1.C([Cu])#N.[Li+].[Cl-].Cl>C1COCC1.[Cu].[Zn].[Zn].CC(O)=O>[N+:1]([CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:10][CH2:11][CH:12]1[O:17][CH2:16][CH2:15][CH2:14][O:13]1)([O-:3])=[O:2]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 10920477Cyclopentene, 1-nitro-HCID 11021059HCID 11021059, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 20087862HCID 20087862, compoundYield 85.3%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 10290809Zinc copper coupleCatalystHCID 176Acetic AcidSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

At -78° C., add 1-nitrocyclopentene (1.8 ml, 18.4 mmol) in THF (20 ml) to a THF solution (33 ml) of the zinc-copper reagent prepared from 2-(2-iodoethyl)-1,3-dioxane (5.6 gm, 23 mm), zinc powder (1.58 g), CuCN (1.9 g) and LiCl (1.7 g), according to the general procedure of P. Knochel et. al. (J, Org. Chem. 1989, 54, 5200). After 15 min. warm to 0° C. for one hour, then recool to -78° C. and add AcOH (2.0 ml). Warm to RT, add AcOH:0.1N HCl (15 ml, 1:2) and stir for one hr. Partition between EtOAc and brine. Concentrate the organic layer and purify by silica gel chromatography using EtOAc/Hex 1:3 to elute the title compound (3.6 g 15.7 mmol) as an oil. CI MS: M+1=230.

Workup

  1. customrecool to -78° C.
  2. temperatureWarm to RT
  3. customPartition between EtOAc and brine
  4. concentrationConcentrate the organic layer
  5. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-80643ab861424fcb8acac6f6b605b21a
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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