Tributylphosphine → methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-oxopropanoate

HRID 922325Notes

Reaction equation

HRID 922325 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)\[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)\[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 508465Methyl (4-Hydroxybenzoyl)acetateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 87106340methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-oxopropanoateYield 14%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged 10 mL of Toluene. to the stirred solvent was added methyl 3-(4-hydroxyphenyl)-3-oxopropanoate (0.2 g, 1.036 mmol) and (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.22 g, 0.82 mmol) was added Tributyl phosphine (0.271 g, 1.324 mmol) and 1,1′-(Azodicarbonyl)di-Piperidine portion wise at 0° C. (0.339 g, 1.346 mmol). Then the reaction mixture was stirred at RT for 12 h. After completion of the reaction (reaction monitored by TLC), reaction mixture was concentrated and extracted with ethyl acetate. Then the organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, and the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent (0.05 g Yield: 14%) MS (ESI, 120 eV): m/z=448.1 (M+H)+.

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC), reaction mixture
  3. concentrationwas concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure
  7. customthe resulting crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b2cfdaeae00144a0bd511a0e2d79d88c
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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