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

HRID 1373693
ノート
印刷プレビュー

反応式

HRID 1373693 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒

4
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 10311-Propanol溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-606677831ed448d3a23675acd076e7ff
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07163932B2

反応ノート

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