Methylparaben → Methyl 4-[(5-bromo-2-ethylthiophen-3-yl)(cyclohexyl)methoxy]benzoate

HRID 1877003Notes

Reaction equation

HRID 1877003 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][CH3:8])=[C:4]([CH:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[OH:10])[CH:3]=1.O[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([CH2:7][CH3:8])=[C:4]([CH:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:10][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 68509731(5-Bromo-2-ethylthiophen-3-yl)(cyclohexyl)methanol

Product 1

HCID 68516383Methyl 4-[(5-bromo-2-ethylthiophen-3-yl)(cyclohexyl)methoxy]benzoateYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (5-bromo-2-ethylthiophen-3-yl)(cyclohexyl)methanol (1.50 g) synthesized above, methyl 4-hydroxybenzoate (904 mg), 1,1′-(azodicarbonyl)dipiperidine (2.50 g) and tetrahydrofuran (30 mL) was added tributylphosphine (2.47 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the precipitate was removed by filtration and washed with diisopropyl ether. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title compound (1.20 g, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe precipitate was removed by filtration
  3. washwashed with diisopropyl ether
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)

Sources & evidence

ORD record
ord-3a674dfff25749f49e9ad36d0c7fa8fd
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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