Triphenylphosphine → HCID 59272912, compound

HRID 1526150Notes

Reaction equation

HRID 1526150 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>C(Cl)Cl>[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 DCM (250 ml) and then cooled to 0° C. Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to r.t. and shaken for 2 h. The resin was filtered off and washed with DCM. The combined filtrates were evaporated to dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D27 as colorless oil (5.38 g, 95%).

Workup

  1. additionDi-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise
  2. temperaturethe reaction mixture was warmed to r.t.
  3. filtrationThe resin was filtered off
  4. washwashed with DCM
  5. customThe combined filtrates were evaporated to dryness
  6. customThe crude product thus obtained
  7. customwas purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%)
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c72b9c6d6ec410fbe68e4681587c3a3
Source dataset
uspto-grants-2015_07
Patent number
US09085577B2

Reaction notes

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