tert-Butanol → HCID 11746573, compound

HRID 377948Notes

Reaction equation

HRID 377948 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][C:22](O)([CH3:24])[CH3:23]>CN(C1C=CN=CC=1)C.C1C=CC=CC=1>[C:1]([CH2:9][CH2:10][C:11]([O:13][C:22]([CH3:24])([CH3:23])[CH3:21])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 728713-Benzoylpropionic acid

Product 1

HCID 11746573HCID 11746573, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

Once the 3-benzoylpropionic acid had dissolved, then 6.1 mL (0.0830 mol) of triethylamine was added. The solution was stirred for 6 hours, after which the THF solution was filtered to remove the triethylamine hydrochloride. The filtrate was rotoevaporated to yield a light beige solid. To this solid was added 200 mL of benzene followed by 6.0 mL (0.104 mol) of 2-methyl-2-propanol and the mixture was stirred with heating to dissolve all of the solid. After complete dissolution, 5.40 g (0.0442 mol) of DMAP was added to the solution. The solution immediately turned dark red and was stirred at room temperature for 36 hours. The solution was washed with 10% aqueous HCl solution, followed by 2×5% aq. NaOH solution and finally with water. The organic layer was then dried (MgSO4), filtered and concentrated. The resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes) and the resultant oil obtained was distilled under reduced pressure to yield 6.45 g (64%) of t-butyl 3-benzoylpropionate as a colorless oil. lit bp 129-130° C. at 1.5 mm Hg.; 1HNMR ppm (δ), CDCL3 7.98 (d, 2H), 7.54 (m, 1H), 7.46 (m, 2H), 3.26 (t, 2H), 2.68 (t, 2H), 1.45 (s, 9H). 13CNMR ppm (δ), CDCl3, 198.3 (C=O), 172.1 (CO2), 136.7 (q), 133.0, 128.6, 128.0, 80.6 (C(CH3)3), 33.5, 29.4, 28.0 (CH3).

Workup

  1. filtrationafter which the THF solution was filtered
  2. customto remove the triethylamine hydrochloride
  3. customto yield a light beige solid
  4. stirringthe mixture was stirred
  5. temperaturewith heating
  6. dissolutionto dissolve all of the solid
  7. additionwas added to the solution
  8. stirringThe solution immediately turned dark red and was stirred at room temperature for 36 hours
  9. washThe solution was washed with 10% aqueous HCl solution
  10. dry with materialThe organic layer was then dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes)
  14. customthe resultant oil obtained
  15. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-9a017f778aa348628ace344fd36078e6
Source dataset
uspto-grants-2000_02
Patent number
US06028224

Reaction notes

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