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4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehyde → 1-(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)-2-methyl-2-propen-1-ol

HRID 1662532
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HRID 1662532 반응식
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:23]=[O:24])[C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:12][CH:13]=1)([CH3:4])[CH3:3].[C:27]([Mg]Br)([CH3:29])=[CH2:28]>C1COCC1>[CH3:4][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23]([OH:24])[C:27]([CH3:29])=[CH2:28])[CH:9]=1)([CH3:1])[CH3:3]
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참가 물질

4

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HCID 577066184-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehydeHCID 178456138HCID 178456138, 화합물

생성물 1

HCID 577055531-(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)-2-methyl-2-propen-1-ol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A 250 mL round bottom flask was charged with 83.18C (1.05 g, 2.80 mmol) and THF (15 mL) and cooled to −78° C. under N2. To the cold solution was added isopropenylmagnesium bromide (0.5 M in THF) (available from Aldrich) (11.2 mL, 5.61 mmol) dropwise. The mixture was stirred for 30 minutes at −78° C. The cooling bath was removed, and the mixture was stirred for 30 minutes at ambient temperature. The reaction was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-15% EtOAc/hexane) to afford 83.18D (1.05 g, 90% yield) as a colorless oil.

후처리

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred for 30 minutes at ambient temperature
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. additiondiluted with EtOAc
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash chromatography (0-15% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-d7580650ea614659a0947b66bb26ff6f
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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