Triphenylphosphine → HCID 87106278, compound

HRID 922282Notes

Reaction equation

HRID 922282 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)\[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.O[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:34][CH2:35][CH3:36])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)\[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH2:34][CH2:35][CH3:36])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 66685333HCID 66685333, compoundHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 87106278HCID 87106278, compoundYield 21.74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged dry THF (5.0 mL) and (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.134 g, 0.5 mmol). To the above mixture methyl 3-(4-hydroxyphenyl)hexanoate (0.11 g, 0.5 mmol) was added and the resulting mixture stirred at 0° C. for 5 min. Triphenyl phosphine (0.17 g, 0.65 mmol) was added to the mixture and stirred at 0° C. for 15 min followed by the addition of diethylazadicarboxylate (0.13 g, 0.65 mmol). After stirring the resulting mixture at RT for 16 h, the RM was evaporated to remove the THF. The residue was diluted with water (15 mL) and extracted with ethyl acetate (15 mL×2). The organic layer was washed with saturated brine solution (15 mL) and dried over anhydrous Na2SO4. Concentration of the solvent and purification of the resulting residue by column chromatography on silica gel (100/200 mesh), using petroleum ether and ethyl acetate as eluent, gave the product (0.05 g, yield: 21.74%)

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. stirringstirred at 0° C. for 15 min
  3. additionfollowed by the addition of diethylazadicarboxylate (0.13 g, 0.65 mmol)
  4. stirringAfter stirring the resulting mixture at RT for 16 h
  5. customthe RM was evaporated
  6. customto remove the THF
  7. additionThe residue was diluted with water (15 mL)
  8. extractionextracted with ethyl acetate (15 mL×2)
  9. washThe organic layer was washed with saturated brine solution (15 mL)
  10. dry with materialdried over anhydrous Na2SO4
  11. customConcentration of the solvent and purification of the resulting residue by column chromatography on silica gel (100/200 mesh)

Sources & evidence

ORD record
ord-3adcb36ed53a404fa956e2527a522925
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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