Water → Bis(thien-2-yl)mono(4-methoxyphenyl)methanol

HRID 1450050ノート

反応式

HRID 1450050 の反応式
Br[CH2:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[O:21].O>C1COCC1.CCCCCCC.CCOC(C)=O.CCOCC>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)[OH:21]

参加物

8

反応物 4

HCID 962WaterHCID 697132-Thienyl ketoneHCID 13097734p-Bromo methoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 18943083Bis(thien-2-yl)mono(4-methoxyphenyl)methanol

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 21899848Ethylacetate heptane溶媒

実験手順

p-Bromo methoxybenzene (0.96 g, 5.2 mmol) was dissolved in THF (50 mL) and n-butyl lithium (2.08 mL, 2.5M in toluene) was added at -70° C. and stirred at this temperature for 10 minutes when the thienyl ketone (1.0 g 5.2 mmol) (see JACS 74: 1733-36 (1952), JCS 1956, 698-705 and Receuil 68: 24 (1949)) dissolved in THF (5 mL) was added. The temperature was allowed to rise gradually to room temperature over night. The mixture was hydrolysed with water (50 mL). Ether (150 mL) was added and the phases were separated, the aqueous phase was extracted with more ether (100 mL) and the combined organic phase was washed with water (70 mL), dried (MgSO4) and the solvent evaporated leaving a semicrystalline black residue. The black residue was dissolved in hot heptane/EtOAc (3:1) and chromatographed on a column of alumina with heptane:EtOAc 3:1 as eluent. The product was isolated in a yield of 0.72 g (46.0%).

後処理

  1. additionwas added
  2. waitto rise gradually to room temperature over night
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with more ether (100 mL)
  5. washthe combined organic phase was washed with water (70 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customleaving a semicrystalline black residue
  9. customchromatographed on a column of alumina with heptane:EtOAc 3:1 as eluent
  10. customThe product was isolated in a yield of 0.72 g (46.0%)

出典と根拠

ORDレコード
ord-7a29e28b93f24916a29032f360805780
出典データセット
uspto-grants-1997_02
特許番号
US05599522

反応ノート

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