Acetone → 7-(4-Fluorophenyl)-7-(6-hydroxy-3-hydroxymethyl-2,4,5-trimethylphenyl)heptanoic acid

HRID 373381ノート

反応式

HRID 373381 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH:26]=[O:27])[C:18]=2[CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:17]2[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH2:26][OH:27])[C:18]=2[CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 151251387-(4-Fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

生成物 1

HCID 199361647-(4-Fluorophenyl)-7-(6-hydroxy-3-hydroxymethyl-2,4,5-trimethylphenyl)heptanoic acid収率 40.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (1.8 g) in tetrahydrofuran (30 ml) was added sodium borohydride (176 mg) at 0° C. and the mixture was stirred at room temperature for 2 hours. Acetone was added and the solvent was distilled off under reduced pressure. Water and ethyl acetate were added and the organic layer was separated. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crystals. They were recrystallized from acetonitrile to obtain 7-(4-fluorophenyl)-7-(6-hydroxy-3-hydroxymethyl-2,4,5-trimethylphenyl)heptanoic acid (740 mg) (Compound 32). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

後処理

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater and ethyl acetate were added
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto obtain crystals
  8. customThey were recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-8a0ee245e75b40c6aa77fdf77a8510f8
出典データセット
uspto-grants-1992_11
特許番号
US05162571

反応ノート

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