Triphenylphosphine → HCID 59272912, compound

HRID 2401679Notes

Reaction equation

HRID 2401679 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[O:10]1[CH2:15][CH2:14][CH:13](O)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 198594-Bromo-2-chlorophenolHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 59272912HCID 59272912, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in dichloromethane (250 ml) and then cooled to 0° C. Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to room temperature and shaken for 2 hours. The resin was filtered off and washed with dichloromethane. The combined filtrates were evaporated till dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2%). The desired fractions were collected and evaporated in vacuo to yield intermediate 14 as a colorless oil (5.38 g, 95%).

Workup

  1. additionDi-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise
  2. temperaturethe reaction mixture was warmed to room temperature
  3. filtrationThe resin was filtered off
  4. washwashed with dichloromethane
  5. customThe combined filtrates were evaporated till dryness
  6. customThe crude product thus obtained
  7. customwas purified by column chromatography (silica gel
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-2ab5ae8bae324ce8b3552afa7eb8a7b2
Source dataset
uspto-grants-2014_08
Patent number
US08796311B2

Reaction notes

Loading…