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

HRID 2243293
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HRID 2243293 반응식
[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]
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참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23118874Methyl(E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f5132f2afa3d4d319522aad048a5c249
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07674825B2

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