Hydrogen Peroxide → HCID 86713397, compound

HRID 595035Notes

Reaction equation

HRID 595035 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.N1C=NN=N1.C(N(CC)[P:21]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])C.[OH:34]O>C(#N)C.C(Cl)Cl>[C:28]([O:27][P:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:34])([CH3:29])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 178418441HCID 178418441, compound

Product 1

HCID 86713397HCID 86713397, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 2-(4-hydroxyphenyl)acetate (1.80 g, 10.83 mmol) in acetonitrile (35 mL) was added 1H-tetrazole (3% 1H-tetrazole in MeCN, 65.0 mL, 22.1 mmol), followed by di-tert-butyl diethylphosphoramidite (5.91 g, 23.70 mmol). The reaction mixture was stirred at room temperature for 35 min and concentrated to give a solid. To this solid in 50 mL of DCM was added 30% H2O2 (30 mL). The resulting mixture was stirred at room temperature for 30 min and diluted with DCM. The organic phase was separated, washed sequentially with water, saturated NaHCO3 solution, and brine, then concentrated. The residue was purified by silica gel chromatography (hexane/EtOAc) to afford Preparation 44B (3.94 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.25-7.14 (m, 4H), 3.69 (s, 3H), 3.59 (s, 2H), 1.51 (s, 18H).

Workup

  1. concentrationconcentrated
  2. customto give a solid
  3. stirringThe resulting mixture was stirred at room temperature for 30 min
  4. customThe organic phase was separated
  5. washwashed sequentially with water, saturated NaHCO3 solution, and brine
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (hexane/EtOAc)
  8. customto afford

Sources & evidence

ORD record
ord-0130b7e787a642b69a90158ee6b6c2d2
Source dataset
uspto-grants-2016_01
Patent number
US09242941B2

Reaction notes

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