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Diethylamine → (3'-Methanesulfonyl-biphenyl-4-yl)-methanol

HRID 1373693
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HRID 1373693 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(CC)CC.C([O-])(O)=O.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(O)CC>[CH3:11][S:8]([C:4]1[CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-

생성물 1

HCID 21879230(3'-Methanesulfonyl-biphenyl-4-yl)-methanol수율 95.5%

시약·촉매·용매

4
HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 10311-Propanol용매HCID 1140Toluene용매

실험 절차

To a degassed solution of the product of step 1 (5.7 g, 24.2 mmol,), and 4-hydroxymethylphenylboronic acid (5.47 g, 36 mmol) in toluene (150 mL) was added Pd2(dba)3 (1.09 g, 1.2 mmol). The mixture was degassed and Ph3P (2.5 g, 9.6 mmol), Et2NH (2.63 g, 36 mmol), n-propanol (18 mL) and H2O (18 mL) was added. The mixture was heated to reflux for 26 h. Aqueous NaHCO3 was added and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 6.06 g (95%) of the title compound.

후처리

  1. customThe mixture was degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 26 h
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (anhyd. MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-606677831ed448d3a23675acd076e7ff
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07163932B2

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