tert-Butanol → HCID 13265131, compound

HRID 1640003Notes

Reaction equation

HRID 1640003 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C1C=CC=CN=1)C.[C:24](O)([CH3:27])([CH3:26])[CH3:25].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:14])[C:11]([O:13][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 218852-DimethylaminopyridineHCID 892442-(4-Nitrophenyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 13265131HCID 13265131, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(4-nitrophenyl)propanoic acid (15.0 g, 76.9 mmol), dimethylaminopyridine (4.70 g, 38.4 mmol) and tert-butanol (8.10 mL, 84.6 mmol) in methylene chloride (300 mL) was stirred at 0° C. for 2 h. After this time, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (17.0 g, 84.6 mmol) was added and the reaction stirred for a further 2 h. The ice bath was then removed and the reaction left to stir at room temperature overnight. After this time, the solvents were concentrated under reduced pressure and the solids redissolved in ethyl acetate (200 mL). The organic layer was then washed with saturated sodium bicarbonate (200 mL), 1 M citric acid (200 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica, 1:20 ethyl acetate/hexanes) afforded tert-butyl 2-(4-nitrophenyl)propanoate (14.4 g, 75%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=9.2 Hz, 2H), 7.46 (d, J=9.2 Hz, 2H), 3.73 (q, J=7.1 Hz, 1i), 1.49 (d, J=7.1 Hz, 3H), 1.40 (s, 9H).

Workup

  1. stirringthe reaction stirred for a further 2 h
  2. customThe ice bath was then removed
  3. waitthe reaction left
  4. stirringto stir at room temperature overnight
  5. concentrationAfter this time, the solvents were concentrated under reduced pressure
  6. dissolutionthe solids redissolved in ethyl acetate (200 mL)
  7. washThe organic layer was then washed with saturated sodium bicarbonate (200 mL), 1 M citric acid (200 mL) and brine (200 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by flash chromatography (silica, 1:20 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-69f09662957348aa89c2cbf1fe611ce0
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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