Triphenylphosphine → HCID 66790094, compound

HRID 1510114Notes

Reaction equation

HRID 1510114 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C@@H:12](O)([CH2:14][CH3:15])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:13][C@@H:12]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 444683(+)-2-ButanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 66790094HCID 66790094, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 0° C. solution of methyl 3-hydroxybenzoate (5.00 g, 32.9 mmol) in toluene (32.9 ml) was added (S)-(+)-sec-butanol (3.34 ml, 36.1 mmol), triphenylphosphine (9.48 g, 36.1 mmol), and DIAD (7.03 ml, 36.1 mmol). After warming to rt overnight, the reaction mixture was filtered through a fritted funnel and washed with toluene. The filtrate was concentrated. The residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 10% EtOAc/hexanes) to give the desired product.

Workup

  1. filtrationthe reaction mixture was filtered through a fritted funnel
  2. washwashed with toluene
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-583bf307726b4d8fa137494ecd396324
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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