Dichloromethane → HCID 15086794, compound

HRID 1534556Notes

Reaction equation

HRID 1534556 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10].Cl[CH2:12]Cl.[N+](=C)=[N-]>CCOCC>[CH3:12][O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9550DiazomethaneHCID 15046660HCID 15046660, compound

Product 1

HCID 15086794HCID 15086794, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.0 g of (S)-3-hydroxy-1-(2-propynyl)-2-pyrrolidinone, 70 g of silica gel and 200 ml of dichloromethane was cooled in an ice bath. A 300 ml solution of diazomethane in ether was added portionwise. The reaction was filtered, washed with methanol and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving 700 mg of (S)-3-methoxy-1-(2-propynyl)-2-pyrrolidinone, [α]D26 =-71° (dichloromethane).

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationThe reaction was filtered
  3. washwashed with methanol
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-342fc7fec4154a8d940eecd67dfdccc2
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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