M-Cresol → HCID 51924568, compound

HRID 2170704Notes

Reaction equation

HRID 2170704 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O:31]C(/N=N/C(OC(C)C)=O)=O)C.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>CCOC(C)=O>[C:2]1([CH3:8])[CH:3]=[CH:4][CH:5]=[C:6]([O:7][C@@H:43]([CH3:42])[C:44]([O:45][CH3:46])=[O:31])[CH:1]=1

Participants

6

Reactant 4

HCID 342M-CresolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 51924568HCID 51924568, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of m-cresol (5.0 g, 46 mmol, 1 equiv), methyl-D(+) lactate (4.8 g, 46 mmol, 1 equiv) and PPh3 (14.5 g, 55.2 mmol, 1.2 equiv) in anhydrous THF (200 mL) under argon and at 0° C., was added dropwise DIAD (9.96 g, 48.2 mmol, 1.5 equiv). The reaction mixture was stirred at 0° C. until room temperature overnight. The crude mixture was dissolved in AcOEt (200 mL) and washed with a 0.5 N HCl aqueous solution (×2), a saturated NaHCO3 solution (×2), brine and then dried over Na2SO4. After filtration, solvent was evaporated. The crude product was purified by flash chromatography on silica gel (AcOEt/hexane 0->60%) to obtain the title compound.

Workup

  1. washwashed with a 0.5 N HCl aqueous solution (×2)
  2. dry with materiala saturated NaHCO3 solution (×2), brine and then dried over Na2SO4
  3. filtrationAfter filtration, solvent
  4. customwas evaporated
  5. customThe crude product was purified by flash chromatography on silica gel (AcOEt/hexane 0->60%)

Sources & evidence

ORD record
ord-13485b679b0f4f3fb3fb64e17e59785e
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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