Triphenylphosphine → methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-(1,2-oxazol-3-yl)propanoate

HRID 922202Notes

Reaction equation

HRID 922202 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:18]=[CH:17][O:16][N:15]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:19][O:20]/[N:21]=[C:22](/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)\[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:19][O:20]/[N:21]=[C:22](/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)\[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:14]3[CH:18]=[CH:17][O:16][N:15]=3)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 66684900Methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 87106456methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-(1,2-oxazol-3-yl)propanoateYield 27.47%

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 methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoate (0.18 g, 0.74 mmol). To the above mixture (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.2 g, 0.74 mmol) was added and the resulting mixture stirred at 0° C. for 5 min. Triphenyl phosphine (0.25 g, 0.96 mmol) was added to the mixture and stirred at 0° C. for 15 min followed by the addition of diisopropylazadicarboxylate (0.19 g, 0.96 mmol). After stirring the resulting mixture at RT for 10 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 (60-80) and ethyl acetate (ratio) as eluant, gave the product (0.1 g, yield: 27.47%): MS (ESI, 120 eV): m/z=501.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 8.20 (d, 1H), 7.57-7.60 (t, 2H), 7.22-7.28 (m, 5H), 7.07-7.10 (d, 2H), 6.81-6.85 (m, 4H), 5.99-6.00 (d, 1H), 5.12 (s, 2H), 4.85 (s, 2H), 4.47-4.52 (t, 1H), 3.98 (s, 3H), 3.56 (s, 3H), 3.18-3.26 (q, 1H), 2.82-2.90 (q, 1H).

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 diisopropylazadicarboxylate (0.19 g, 0.96 mmol)
  4. stirringAfter stirring the resulting mixture at RT for 10 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-49581cfa88f442b79ea17e6ad1f222b2
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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