Sodium Carbonate → 2-(3-Thiophen-3-yl-phenyl)-ethanol

HRID 1713672ノート

反応式

HRID 1713672 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].[S:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[C:4]([CH2:5][CH2:6][OH:7])[CH:8]=[CH:9][CH:10]=2)=[CH:12]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 27340902-(3-Bromophenyl)ethan-1-ol

生成物 1

HCID 199171332-(3-Thiophen-3-yl-phenyl)-ethanol

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of 3-bromo-phenethyl-alcohol (1 g, 4.97 mmol), 3-thiophene-boronic-acid (1.9 g, 14.9 mmol, 3.0 equiv), Pd(PPh3)4 (172 mg, 0.149 mmol, 0.03 equiv), and 2M Na2CO3 (10.8 mL, 22.4 mmol, 4.5 equiv) in toluene (40 mL) is heated to reflux 1 h, under an argon atmosphere. The resulting suspension is allowed to cool to RT and filtered through a pad of celite, washing the filter cake with CH2Cl2 and water. The layers are separated. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the crude material by silica gel column chromatography (CH2Cl2/Et2O, 95/5) affords the title compound: ES-MS: 205.0 [M+H]+; single peak at tR=4.27 min (System 2); Rf=0.32 (CH2Cl2/Et2O, 95/5).

後処理

  1. temperatureis heated
  2. temperatureto reflux 1 h, under an argon atmosphere
  3. filtrationfiltered through a pad of celite
  4. washwashing the filter cake with CH2Cl2 and water
  5. customThe layers are separated
  6. washThe organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude material by silica gel column chromatography (CH2Cl2/Et2O, 95/5)

出典と根拠

ORDレコード
ord-c333d8530e324d0e887d6deebcdbac7a
出典データセット
uspto-grants-2010_09
特許番号
US07795288B2

反応ノート

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