Triphenylphosphine → HCID 86688098, compound

HRID 407944Notes

Reaction equation

HRID 407944 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:27][C:28]1[N:33]=[CH:32][C:31](O)=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[Br:27][C:28]1[N:33]=[CH:32][C:31]([O:1][C@H:2]2[CH2:6][CH2:5][O:4][C:3]2=[O:7])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 27628652-Bromo-5-hydroxypyridineHCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-

Product 1

HCID 86688098HCID 86688098, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (R)-3-hydroxydihydrofuran-2(3H)-one (500 mg, 4.9 mmol) in toluene (15 mL) was added triphenylphosphine (1.54 g, 5.88 mmol) and 6-bromopyridin-3-ol (1.02 g, 5.88 mmol). The solution was cooled to 0° C. and degassed with nitrogen bubble for 10 minutes. Di-tert-butyl diazene-1,2-dicarboxylate was dissolved in toluene (5 mL) and added over a 5 minute period. The reaction was allowed to stir for 12 hours with warming to ambient temperature. The reaction was concentrated in vacuo and the resulting material purified by silica gel chromatography eluting 1:1 hexanes/EtOAc to yield (S)-3-(6-bromopyridin-3-yloxy)dihydrofuran-2(3H)-one (1.0 g, 79%) as an off white solid.

Workup

  1. customdegassed with nitrogen
  2. custombubble for 10 minutes
  3. dissolutionDi-tert-butyl diazene-1,2-dicarboxylate was dissolved in toluene (5 mL)
  4. additionadded over a 5 minute period
  5. temperaturewith warming to ambient temperature
  6. concentrationThe reaction was concentrated in vacuo
  7. customthe resulting material purified by silica gel chromatography
  8. washeluting 1:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-cf7dbac727cd4c9f8ea45bcd593f7c7f
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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