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Water → 6-morpholino-3,4-dihydronaphthalen-1(2H)-one

HRID 1362746
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HRID 1362746 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(OCC)(=O)C>[N:20]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1
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참가 물질

9

반응물 4

HCID 962WaterHCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

생성물 1

HCID 131795016-morpholino-3,4-dihydronaphthalen-1(2H)-one수율 95.8%

시약·촉매·용매 4

HCID 2734215
2-(Di-tert-butylphosphino)biphenyl
촉매
HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (3.40 g), morpholine (5.18 g), tripotassium phosphate (3.79 g), tris(dibenzylideneacetone) dipalladium (0) (109 mg) and 2-(di-tert-butylphosphino)biphenyl (71 mg) in 1,2-dimethoxyethane (24 mL) was stirred in a nitrogen atmosphere at 80° C. for one and a half hours. The reaction solution was returned to room temperature, and water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.56 g of the title compound. Properties data of the compound are as follows.

후처리

  1. customwas returned to room temperature
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-6ea7c1d79b4a4b2cbad4d0f01e5846c5
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07880009B2

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