Tributylphosphine → methyl 2-[4-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-methyl-1,2-oxazol-5-yl]acetate

HRID 922245Notes

Reaction equation

HRID 922245 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:18])=[N:10][O:11][C:12]=2[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[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.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O.C1(C)C=CC=CC=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:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:9]([CH3:18])=[N:10][O:11][C:12]=3[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:7]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 86695756Methyl [4-(4-hydroxyphenyl)-3-methyl-1,2-oxazol-5-yl]acetateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 88581611methyl 2-[4-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-methyl-1,2-oxazol-5-yl]acetateYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 50 mL two neck RB flask fitted with magnetic stirrer was charged with 15 mL of toluene. To the stirred solvent were added methyl [4-(4-hydroxyphenyl)-3-methyl-1,2-oxazol-5-yl]acetate (0.3 g, 1.21 mmol), (1Z)-2-[4-(hydroxymethyl)phenoxy]-1-phenylethanone O-methyloxime (0.33 g, 1.21 mmol) and tri-(n-butyl)phosphine (0.39 g, 1.94 mmol) under nitrogen atmosphere. The reaction mixture was cooled to 0° C. and 1,1′-(azodicarbonyl)-dipiperidine (0.49 g, 1.94 mmol) was added portion wise and stirred at room temperature for 2 h. After completion of the reaction, the reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (25 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as eluents. The product was obtained as colorless oil (0.47 g, yield: 77%). 1H NMR (300 MHz, CDCl3): δ 7.57-7.61 (m, 2H), 7.26-7.30 (m, 5H), 7.11-7.14 (d, 2H), 6.94-6.97 (d, 2H), 6.85-6.88 (d, 2H), 5.14 (s, 2H), 4.93 (s, 2H), 3.99 (s, 3H), 3.68 (s, 2H), 3.65 (s, 3H), 2.20 (s, 3H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecaa70cb570745a3ac18c8261b14377e
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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