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

HRID 1896814Notes

Reaction equation

HRID 1896814 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-f48ef6fb83dc43459b4a9a9ec9a83848
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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