Methanol → methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

HRID 37728ノート

反応式

HRID 37728 の反応式
C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@H]23)C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:39])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:25][CH:24]=1.CO>O1CCCC1>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]([OH:39])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 887MethanolHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 19936161Methyl 7-(4-fluorophenyl)-7-oxoheptanoate

生成物 1

HCID 10562892methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate収率 98.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

実験手順

To a solution of (R)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2]oxazaborole (1.1 g) in tetrahydrofuran (20 ml) was added at 0° C. 1M tetrahydrofuran solution of boranetetrahydrofuran complex (4 ml). To this solution were added dropwise a solution of methyl 7-(4-fluorophenyl)-7-oxoheptanoate (10.0 g, 39.6 mmol) in tetrahydrofuran (20 ml) and 1M tetrahydrofuran solution of boranetetrahydrofuran complex (20 ml), simultaneously, taking 25 minutes. The mixture was stirred for 30 minutes at the same temperature range, to which was added methanol (20 ml), followed by stirring for 30 minutes at room temperature. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography to give methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate (9.91 g). Physico-chemical properties and spectral data of this product are shown in [Table 7]. Likewise, Compound 1-2 was prepared.

後処理

  1. stirringby stirring for 30 minutes at room temperature
  2. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-5fdb7b29cd3c48a78d22172e09f3d335
出典データセット
uspto-grants-1995_05
特許番号
US05420363

反応ノート

読み込み中…