Diethyl Ether → 7-(Phenoxy)-1-(5-benzyloxymethyl-1,3,4-oxadiazol-2-yl)-heptan-1-one

HRID 512006Notes

Reaction equation

HRID 512006 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[O:11][CH:12]=[N:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:16][CH2:17][CH2:18][CH3:19].[Mg+2].[Br-].[Br-].[CH3:23][CH2:24][O:25][CH2:26][CH3:27]>>[O:25]([CH2:26][CH2:27][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([C:12]1[O:11][C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:14][N:13]=1)=[O:8])[C:24]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:23]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 82241Magnesium BromideHCID 579994412-[(Benzyloxy)methyl]-1,3,4-oxadiazoleHCID 178418339Butyllithium

Product 1

HCID 250186077-(Phenoxy)-1-(5-benzyloxymethyl-1,3,4-oxadiazol-2-yl)-heptan-1-one

Procedure

The title compound was synthesized analogously to 73.2 (see experimental below), using 72 (190 mg, 1 mmol), n-BuLi (2.5 M solution in hexane, 0.4 mL, 1 mmol), MgBr2.Et2O (284 mg, 1.1 mmol) and 68.1 (132 mg, 0.5 mmol). The crude obtained after workup was chromatographed over a column of silica gel, eluting with 30% ethyl acetate-petroleum ether to give 73.1 as a white solid (m p 61-63° C.) in 53% yield (104 mg).

Workup

  1. customThe title compound was synthesized analogously to 73.2 (see experimental below)
  2. customThe crude obtained after workup
  3. customwas chromatographed over a column of silica gel
  4. washeluting with 30% ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-0695eef21b244e35ac7c1fc796cabf36
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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