Phenol → HCID 178527045, compound

HRID 1993113Notes

Reaction equation

HRID 1993113 reaction equation
[P:1]([O:4][CH:5]([CH3:9])C([O-])=O)(=[O:3])=[O:2].S(Cl)(Cl)=O.C1(O)C=CC=CC=1.N1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.C(Cl)Cl>[CH2:5]([O:4][PH:1](=[O:2])[O:3][CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 1049PyridineHCID 1140TolueneHCID 24386Thionyl ChlorideHCID 131727853Monophospholactate

Product 1

HCID 178527045HCID 178527045, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To the suspension of compound 30 (11.3 g, 30 mmol) in toluene (150 mL) was added thionyl chloride (13 mL, 180 mmol), followed by DMF (a few drops). The reaction mixture was heated at 65° C. for 4.5 hrs, and evaporated under reduced pressure. The mixture was coevaporated with toluene (2×) to afford a brown solid. To the solution of the brown solid in CH2Cl2 (120 ml) at 0° C. was added phenol (11.28 g, 120 mmol), followed by slow addition of pyridine (14.6 mL, 180 mmol). The reaction mixture was allowed to warm to 25° C. and stirred for 14 hrs. Solvents were removed under reduced pressure. The mixture was diluted with EtOAc, and washed with water (3×) and brine (1×), and dried over MgSO4. Concentration gave a dark oil, which was purified by flash column chromatography (hexanes/EtOAc=3/1 to 1/1) to afford compound 31 (9.8 g).

Workup

  1. customevaporated under reduced pressure
  2. customto afford a brown solid
  3. temperatureto warm to 25° C.
  4. customSolvents were removed under reduced pressure
  5. additionThe mixture was diluted with EtOAc
  6. washwashed with water (3×) and brine (1×)
  7. dry with materialdried over MgSO4
  8. concentrationConcentration
  9. customgave a dark oil, which
  10. customwas purified by flash column chromatography (hexanes/EtOAc=3/1 to 1/1)

Sources & evidence

ORD record
ord-35907e34e87a412db26aefd3f97b45ca
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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