Triphenylphosphine → HCID 86662318, compound

HRID 1431072Notes

Reaction equation

HRID 1431072 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:28]1[CH2:30][C@H:29]1[CH2:31]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:31][C@@H:29]2[CH2:30][O:28]2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 8198212-Chloro-5-hydroxypyridineHCID 5460455(+)-GlycidolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 86662318HCID 86662318, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round-bottomed flask, 6-chloropyridin-3-ol (2.116 g, 16.3 mmol), triphenylphosphine (5.14 g, 19.6 mmol) and (R)-oxiran-2-ylmethanol (1.21 g, 1.08 ml, 16.3 mmol) were combined with THF (75.0 ml) to give a colorless solution. Cooled to 0° C. DEAD (3.41 g, 3.1 ml, 19.6 mmol) was added. The reaction mixture was allowed to come to 25° C. and stirred for 30 h. The reaction mixture was concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, 80 g, 5% to 25% EtOAc in hexanes) followed by flash chromatography (silica gel, 40 g, 0.5% to 1% MeOH in DCM) to afford the desired product (1.8 g, 59%) as a white solid. (M+H)+=186 m/e.

Workup

  1. customto give a colorless solution
  2. customto come to 25° C.
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe crude product was purified by flash chromatography (silica gel, 80 g, 5% to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c8c717f3005d4de69bc65f3b04be0cda
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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