Diazomethane → HCID 85913004, compound

HRID 426780Notes

Reaction equation

HRID 426780 reaction equation
[C:1]([O:4][CH:5]1[C:9](=[O:10])[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH2:6]1)(=[O:3])[CH3:2].[N+](=[CH2:22])=[N-]>C(OCC)C>[C:1]([O:4][CH:5]1[C:9](=[O:10])[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:22])=[O:18])=[CH:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 203899457-[4-(Acetyloxy)-5-oxocyclopent-1-en-1-yl]heptanoic acid

Product 1

HCID 85913004HCID 85913004, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (±)-7-[4-acetoxy-5-oxo-cyclopent-1-enyl]heptanoic acid (1.0 g; prepared as described in Example 1) in dry diethyl ether (10 ml) was treated with a solution of diazomethane (0.32 g) in dry diethyl ether (5 ml). The reaction mixture was allowed to stand at ambient temperature for 2.5 hours. The diethyl ether and excess diazomethane were removed in vacuo to yield methyl (±)-7-[4-acetoxy-5-oxocyclopent-1-enyl]heptanoate (1.06 g). [νmax 1740 cm-1, 1720 cm-1, 1625 cm-1, 1380 cm-1, 1240 cm-1 ; λmax (ethanol) 232 mμ; N.M.R. (approximately 10% solution in deuterochloroform); multiplets at 7.28δ, 3.35-2.7δ, 2.7-2.2δ, 2.5-2.0δ, 2.0-1.05δ, doublet of doublets at 5.15δ (J=3 cycles/second and 7 cycles/second), singlets at 3.7δ and 2.1δ.] .

Workup

  1. customThe diethyl ether and excess diazomethane were removed in vacuo

Sources & evidence

ORD record
ord-a0edea824111470d831650896b1d2c5d
Source dataset
uspto-grants-1979_10
Patent number
US04171375

Reaction notes

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