Hydrochloric Acid → HCID 54117308, compound

HRID 377315Notes

Reaction equation

HRID 377315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[Mg].II.C(O[C@H:18]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH2:20][CH2:19]1)(=O)C.Cl>O1CCCC1.[Cu]I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][C@H:18]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH2:20][CH2:19]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 699943-Methoxybenzyl chlorideHCID 5462224MagnesiumHCID 11745606HCID 11745606, compound

Product 1

HCID 54117308HCID 54117308, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A tetrahydrofuran (50 ml) solution of 3-methoxybenzyl chloride (14.01 g) was added slowly to a suspension of magnesium (2.18 g) and iodine (a catalytic amount) in tetrahydrofuran (50 ml) at 60° C. over 40 minutes. After 1 hour stirring at the same temperature, the reaction mixture was cooled to the room temperature. An insoluble material was filtered off and the Grignard solution was prepared. The Grignard solution was added slowly to a suspension of ethyl 5(R)-acetoxy-1-cyclopentenecarboxylate (4.50 g) and copper(I) iodide (0.56 g) in tetrahydrofuran (100 ml) over 1 hour at -60° C. After 1 hour stirring at the same temperature, IN-hydrochloric acid (100 ml) was added to the reaction mixture. The mixture was extracted with ethyl acetate The extract was washed with 1N-hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate and brine. Drying (sodium sulfate) and removal of solvent at reduced pressure followed by flash chromatography over 250 g of silica afforded (-)-ethyl 5(S)-(3-methoxybenzyl)-1-cyclopentencarboxylate as a colorless oil (4.73 g).

Workup

  1. filtrationAn insoluble material was filtered off
  2. customthe Grignard solution was prepared
  3. stirringAfter 1 hour stirring at the same temperature
  4. extractionThe mixture was extracted with ethyl acetate The extract
  5. washwas washed with 1N-hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate and brine
  6. customDrying
  7. custom(sodium sulfate) and removal of solvent at reduced pressure

Sources & evidence

ORD record
ord-ebf48ac99e5c4974978617f1b01632e6
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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