Diazomethane → HCID 13476958, compound

HRID 2164577Notes

Reaction equation

HRID 2164577 reaction equation
[O:1]=[C:2]1[CH:8]2[CH:4]([CH2:5][CH:6]=[C:7]2[C:9]([OH:11])=[O:10])[CH2:3]1.[N+](=[CH2:14])=[N-]>O1CCCC1>[O:1]=[C:2]1[CH:8]2[CH:4]([CH2:5][CH:6]=[C:7]2[C:9]([O:11][CH3:14])=[O:10])[CH2:3]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 134769577-Oxobicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Product 1

HCID 13476958HCID 13476958, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 800 mg of 7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid in 10 mL of tetrahydrofuran was treated at room temperature with ethereal diazomethane. The crude reaction product was purified by chromatographic filtration through 10 g of silica gel (100-200 mesh), eluting with ether petroleum ether, first 2:3 and then 1:1, to afford 560 mg (64%) of methyl 7-oxobicyclo[3.2.0]hept-2-en-2-carboxylate as colorless crystals, mp 58° to 61°. IR (Nujol mull): 1630, 1715, 1790 cm-1 ; NMR (60 MHz, CDCl3): δ 2.5-3.3 (5H, m), 3.75 (3H, s), 4.3-4.6 (1H, m), and 6.90 (1H, broad s). HRMS: Calcd for C9H10O3, 166.0629; found, 166.0633.

Workup

  1. customThe crude reaction product
  2. filtrationwas purified by chromatographic filtration through 10 g of silica gel (100-200 mesh)
  3. washeluting with ether petroleum ether, first 2:3

Sources & evidence

ORD record
ord-beb5b7dd9893495f83e0cb1f35d35869
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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