Hydrochloric Acid → 2-(4-Morpholinophenyl)ethanol

HRID 272698노트

반응식

HRID 272698 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:11]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 728512-(4-Bromophenyl)ethanolHCID 516892Sodium BicarbonateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 135928032-(4-Morpholinophenyl)ethanol수율 50.2%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

A mixture of 2-(4-bromophenyl)ethanol (0.70 mL, 5 mmol), morpholine (0.52 mL, 6 mmol), LHMDS (11 mL, IM solution in THF), Pd2 (dba)3 (46 mg, 0.05 mmol), and CyMAP (24 mg, 0.06 mmol) was heated to reflux for 16 hours. Cooled to room temperature. Acidified with IM HCl, stirred for 10 minutes, and neutralized with saturated NaHCO3. Partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 520 mg (50%) of the desired product. MS (ESI) m/e 208 (M+H)+, 1H NMR (300 MHz, CDCl3): □ 7.15 (d, J=8.48 Hz, 2H), 6.88 (d, J=8.48 Hz, 2H), 3.78-3.87 (m, 6H), 3.11-3.14 (m, 4H), 2.79 (t, J=6.61 Hz, 2H), 1.43 (m, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. customPartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-13264c7218f849018dea5700b0206018
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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