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Ammonium Chloride → Methyl (E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-hydroxy-7-octenoate

HRID 2243293
ノート
印刷プレビュー

反応式

HRID 2243293 の反応式
[BH4-].[Na+].[Si:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:19](=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[NH4+].[Cl-]>CO>[Si:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[CH:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:5])[CH3:4]
参加物反応条件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 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23118874Methyl(E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate

生成物 1

HCID 23118875Methyl (E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-hydroxy-7-octenoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

At 0° C., 0.146 g (3.86 mmol) of sodium borohydride was added to a solution of 1.436 g (3.86 mmol) of CeCl3.7H2O and 3.67 mmol of methyl (E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate from Ex. XIIc in 30 ml of methanol. The mixture was stirred at 0° C. and the progress of the reaction was monitored by thin-layer chromatography. Saturated NH4Cl solution was added, the mixture was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, cyclohexane/EA 10:2). This gave 1.38 g (91.5%) of a colorless liquid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customThe product was purified chromatographically (silica gel, cyclohexane/EA 10:2)

出典と根拠

ORDレコード
ord-f5132f2afa3d4d319522aad048a5c249
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07674825B2

反応ノート

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