Water → 1-[(3-Buten-1-yl)methylphenylsilyl]-3-methyl-1-butanone

HRID 8544

反応式

HRID 8544 の反応式
[CH2:1]([Si:5]([CH3:22])([C:12]1([CH2:18][CH:19]([CH3:21])[CH3:20])SCCCS1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[OH2:23]>CC#N.Cl[Hg]Cl>[CH2:1]([Si:5]([CH3:22])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12](=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:2][CH:3]=[CH2:4]

参加物

5

反応物 2

HCID 962WaterHCID 22967180(3-Buten-1-yl)methyl[2-(2-methyl-1-propyl)-1,3-dithian-2-yl]phenylsilane

生成物 1

HCID 222870621-[(3-Buten-1-yl)methylphenylsilyl]-3-methyl-1-butanone

試薬・触媒・溶媒 2

HCID 24085Mercuric Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 44 (6.19 g, 177 mmol) in CH3CN (200 mL) was added water (10 mL) and HgCl2 (24 g, 88 mmol). After stirring overnight at rt, the mixture was concentrated and partitioned between water (100 mL) and hexane (200 mL). The organic layer was isolated and the aqueous layer extracted twice with 50-mL portions of hexane. The combined organic extracts were washed with saturated aqueous NaCl and dried over Na2SO4. Concennation to dryness in vacuo at rt gave quantitatively crude ketone 45 as a yellow oil. This ketone was used in the next reaction without further purification: Rf=0.75 (1/19 EtOAc:hexane); 1H NMR (300 MHz, CDCl3) δ 7.54–7.51 (m, 2H), 7.41–7.35 (m, 3H), 5.91–5.78 (m, 1H), 4.99 (dd, J=17.0, 1.7 Hz, 1H), 4.90 (dd, J=10.0, 1.7 Hz, 1H), 2.44 (d, J=6.7 Hz, 2H), 2.16–2.06 (m, 3H), 1.16–1.07 (m, 2H), 0.78 (pd. J=6.7 Hz, 6H), 0.51 (s, 3H).

後処理

  1. concentrationthe mixture was concentrated
  2. custompartitioned between water (100 mL) and hexane (200 mL)
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer extracted twice with 50-mL portions of hexane
  5. washThe combined organic extracts were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-944f1193a82d4416b583f12b44d9cb7f
出典データセット
uspto-grants-2006_08
特許番号
US07087776B2

関連ノート

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