Azetidine → 8-(2,5-Dihydrofuran-2-yl)-1,4-dioxaspiro[4.5]decane

HRID 2175497Notes

Reaction equation

HRID 2175497 reaction equation
[CH2:1]([O:4][CH:5]([CH:8]1[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1)[CH:6]=[CH2:7])C=C.N1CCC1>C(Cl)Cl>[O:4]1[CH2:1][CH:7]=[CH:6][CH:5]1[CH:8]1[CH2:9][CH2:10][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 585627078-(1-(Allyloxy)allyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 585628548-(2,5-Dihydrofuran-2-yl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 8-(1-(allyloxy)allyl)-1,4-dioxaspiro[4.5]decane (347 mg, 1.46 mmol), prepared in the previous step, and the Grubbs Generation II catalyst (62 mg, 0.07 mmol) in DCM was degassed and heated to 40° C. under argon for 4 hours. After extraction with saturated NaHCO3 solution, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, ether) to afford the product.

Workup

  1. extractionAfter extraction with saturated NaHCO3 solution
  2. concentrationthe organic layer was concentrated in vacuo
  3. customthe residue purified by flash chromatography (silica gel, ether)
  4. customto afford the product

Sources & evidence

ORD record
ord-372834dfca254222b916975cc9380661
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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