Triphenylphosphine → HCID 86639882, compound

HRID 2040818Notes

Reaction equation

HRID 2040818 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([CH2:21][CH3:22])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:23])[C:4]=1[OH:24])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:44]1[O:46][C@H:45]1[CH2:47]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:21]([C:16]1[CH:15]=[C:14]([C:12]2[O:11][N:10]=[C:9]([C:7]3[CH:6]=[C:5]([CH3:23])[C:4]([O:24][CH2:47][C@H:45]4[CH2:44][O:46]4)=[C:3]([CH2:1][CH3:2])[CH:8]=3)[N:13]=2)[CH:19]=[C:18]([CH3:20])[N:17]=1)[CH3:22]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 6973630(-)-GlycidolHCID 136360510HCID 136360510, compound

Product 1

HCID 86639882HCID 86639882, compoundYield 114.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-4-[5-(2-ethyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol (150 mg, 0.464 mmol) in THF (10 mL), PPh3 (146 mg, 0.557 mmol) and (S)-glycidol (52 mg, 0.696 mmol) is added. The mixture is cooled to 0° C. before DEAD (303 mg, 0.696 mmol, 320 μL of a 40% solution in toluene) is added. The mixture is warmed to rt and stirred for 1 h. The solvent is evaporated and the residue is purified by chromatography on prep. TLC plates with heptane:EA 1:1 to give (R)-2-ethyl-4-[3-(3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (201 mg) as a white solid; LC-MS*: tR=1.10* min; [M+1]+=380.42.

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. customthe residue is purified by chromatography on prep

Sources & evidence

ORD record
ord-c03371d88f6a46c09e61230c7a28d4fc
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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