Triphenylphosphine → HCID 40647465, compound

HRID 2170646Notes

Reaction equation

HRID 2170646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:30]([CH3:35])[C:31]([O:33][CH3:34])=[O:32].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C@@H:30]([CH3:35])[C:31]([O:33][CH3:34])=[O:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 120082-Chloro-5-methylphenolHCID 637514(+)-Methyl lactateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 40647465HCID 40647465, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 2-chloro-5-methylphenol (4.0 g, 28 mmol) in anhydrous THF (24 mL) at 0° C. under argon protection was added triphenylphosphine (9.5 g, 36.4 mmol), followed by addition of the (R)-methyl 2-hydroxypropanoate (3.89 g, 31 mmol). Then DIAD (8.2 mL, 42 mmol) was added slowly to the solution at 0° C. The reaction mixture was stirred at room temperature for 20 h. The solvent was removed and the crude was purified by flash chromatography (AcOEt/hexane 0˜30%) to obtain the title compound.

Workup

  1. customThe solvent was removed
  2. customthe crude was purified by flash chromatography (AcOEt/hexane 0˜30%)

Sources & evidence

ORD record
ord-6e2e66da747044f198debbc70dc6f49b
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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