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Hydrochloric Acid → (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

HRID 1707815
ノート
印刷プレビュー

反応式

HRID 1707815 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[C:23]([OH:24])=[C:22]([CH3:25])[C:21]([CH3:26])=[C:20]([CH:27]=[O:28])[C:19]=2[CH3:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:18]2[C:23]([OH:24])=[C:22]([CH3:25])[C:21]([CH3:26])=[C:20]([CH:27]=[O:28])[C:19]=2[CH3:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10644683methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate

生成物 1

HCID 10524208(R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid収率 90.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate (0.55 g, 1.4 mmol) in tetrahydrofuran (6 ml) was added, under argon atmosphere, 1N sodium hydroxide (2.9 ml). The mixture was stirred for 14 hours at room temperature, to which was added 1N hydrochloric acid (2.9 ml), followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from acetonitrile to give (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (0.49 g). Physico-chemical properties and spectral data of this product were shown in [Table 4]. Likewise, Compounds 26, 28, 30 and 31 were prepared.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-30056d7a3e6a436db74aeee812966557
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05354913

反応ノート

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