Ethyl diazoacetate → HCID 21502421, compound

HRID 1288526Notes

Reaction equation

HRID 1288526 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[CH:14]1([OH:19])CC=C[CH2:15]1.[N+](=[CH:22][C:23](OCC)=O)=[N-]>[Cu]>[O:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]1[O:7][CH:2]1[CH2:23][CH:22]2[CH:4]([CH:5]2[C:6]([O:19][CH2:14][CH3:15])=[O:1])[CH2:3]1

Participants

5

Reactant 3

HCID 12192Ethyl diazoacetateHCID 263182Tetrahydropyranyl etherHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 21502421HCID 21502421, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 0.01 M of the tetrahydropyranyl ether of 3-cyclopentenol (VII) and 1 g. of copper powder is stirred vigorously and maintained at 100° C. while 0.07 M (8 g.) of ethyl diazoacetate is added over a period of 8 hours. The reaction mixture is then extracted with hexane and chromatographed over aluminum oxide (activity I). Elution first with hexane, and then benzene, and evaporation of the eluates gives ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylate (VIII) in 55% yield as a liquid, b.p. 133° at 1.1 mm.; λ max. 195 mmμ (pentane); γ 3100, 3075, 3047, 1725, 1272, 1140 and 1020 cm-1.; δ 3.92 (quartet), 1.07 (triplet) p.p.m.

Workup

  1. additionis added over a period of 8 hours
  2. extractionThe reaction mixture is then extracted with hexane
  3. customchromatographed over aluminum oxide (activity I)
  4. washElution first with hexane
  5. custombenzene, and evaporation of the eluates

Sources & evidence

ORD record
ord-0a4fc9aa074e4939a92ba9bb14b7a29c
Source dataset
uspto-grants-1976_10
Patent number
US03988372

Reaction notes

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