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

HRID 8544

반응식

HRID 8544 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24085Mercuric Chloride촉매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-944f1193a82d4416b583f12b44d9cb7f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087776B2

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