Pyridine → HCID 66905273, compound

HRID 1751524Notes

Reaction equation

HRID 1751524 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.N1C=CC=CC=1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14]>C1COCC1>[O:1]1[CH2:4][CH:3]([O:5][C:13](=[O:14])[O:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 9942117Oxetan-3-ol

Product 1

HCID 66905273HCID 66905273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Oxetan-3-ol (0.100 g, 1.35 mmol) and pyridine (0.13 mL, 1.62 mmol) in THF (2.5 mL) was cooled to 0° C. with an external ice bath, stirring. A solution of 4-Nitrophenyl chloroformate (0.299 g, 1.485 mmol) in THF (2 mL) was added at 0° C. and the solution was allowed to warm to room temperature. The crude reaction was purified by normal phase silica gel (0-100% ethyl acetate:hexanes) chromatography to give Carbonic acid 4-nitro-phenyl ester oxetan-3-yl ester. LCMS-ESI+: calc'd for C10H9NO6: 239.04 (M+); Found: 239.97 (M+H+).

Workup

  1. customThe crude reaction
  2. customwas purified by normal phase silica gel (0-100% ethyl acetate:hexanes) chromatography

Sources & evidence

ORD record
ord-a3c4f4c6ebeb4c4594399ced057ecd49
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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