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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
ノート
印刷プレビュー

反応式

HRID 1662532 の反応式
[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]
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

4

反応物 2

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

生成物 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-ol収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d7580650ea614659a0947b66bb26ff6f
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030354B2

反応ノート

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