Borane → 2-(2,4-Dimethylphenyl)ethanol
反応式
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH2:4]O.B.C1C[O:15][CH2:14]C1>>[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH2:4][CH2:14][OH:15]参加物
4
実験手順
A solution of carboxylic acid 9 (3.40 g; 17.87 mmol) in THF (100 ml) was cooled to 0° C. and treated with 35 ml of a 1.0M solution of borane in THF. After stirring this mixture overnight it was quenched with 1N HCl and the product was extracted into ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of solvent. The crude product was filtered through a plug of silica gel eluting with 20% ethyl acetate in hexane to obtain 2.75 g (quantitative yield) of the product as a clear light oil. 1H NMR (CDCl3): δ2.25, 2.28 (s, 3H each); 2.88 (t, 2H); 3.78 (t, 2H); 6.97-7.07 (m, 3H). IR (neat): 3340, 2947, 1504, 1448, 1265, 1044 cm-1.
後処理
- customwas quenched with 1N HCl
- extractionthe product was extracted into ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialdried (MgSO4)
- filtrationThe crude product was filtered through a plug of silica gel eluting with 20% ethyl acetate in hexane
出典と根拠
- ORDレコード
- ord-7816546a6ee84e31a3ee5df968feb920
- 出典データセット
- uspto-grants-1994_11
- 特許番号
- US05364876
反応ノート
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