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

HRID 37722
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HRID 37722 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b547b57b9c346459835b9df96e10c59
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05420363

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