M-Cresol → HCID 51924569, compound

HRID 2170632Notes

Reaction equation

HRID 2170632 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@@H:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[C:2]1([CH3:8])[CH:3]=[CH:4][CH:5]=[C:6]([O:7][C@H:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])[CH:1]=1

Participants

7

Reactant 4

HCID 342M-CresolHCID 11776TriphenylphosphineHCID 94386methyl (S)-lactateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 51924569HCID 51924569, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the m-cresol (1.0 g, 9.2 mmol) in anhydrous THF (15 mL) at 0° C. under argon protection was added triphenylphosphine (2.55 g, 9.7 mmol), followed by addition of the (S)-methyl 2-hydroxypropanoate (926 μL, 9.7 mmol). Then diisopropylazodicarboxylate (DIAD) (2.85 mL, 13.8 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature overnight. The resulting mixture was diluted by ethyl acetate, washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated. The obtained oil was purified by flash chromatography (Hexane/Ethyl acetate 0˜50%) to afford a colorless oil (820 mg, 46%).

Workup

  1. washwashed with a 0.5 N HCl solution
  2. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  3. concentrationconcentrated
  4. customThe obtained oil was purified by flash chromatography (Hexane/Ethyl acetate 0˜50%)

Sources & evidence

ORD record
ord-8ddc476fba67445c9267aa79d004423f
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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