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

HRID 962821Notes

Reaction equation

HRID 962821 reaction equation
[CH2:1]([Si:5]([C:18]1([CH2:24][CH:25]([CH3:27])[CH3:26])SCCCS1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[OH2:28]>CC#N.Cl[Hg]Cl>[CH2:1]([Si:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:18](=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 2

HCID 962WaterHCID 22287058(3-Buten-1-yl) [2-(2-methyl-1-propyl)-1,3-dithian-2-yl]diphenylsilane

Product 1

HCID 153498501-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanoneYield 88%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 26 (4.64 g 11.2 mmol) in CH3CN (300 nmL) was added water (10 mL) and HgCl2 (15.26 g, 56.21 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 with hexane (50 mL). The combined organic extracts were washed with saturated aqueous NaCl and dried over Na2SO4. Concentration to dryness in vacuo at rt gave crude ketone 33 as a yellow oil (3.2 g, 88%): R.function. =0.80 (1/9 EtOAc:hexane); 1H NMR (300 MHz, CDCl3) δ7.58 (d, J=6.4 Hz, 4H), 7.44 (m, 6H), 5.88 (m, IH), 4.99 (dd, J=17.1, 1.6 Hz, 1H), 4.91 (dd, J=10.2, 1.6 Hz, 1H), 2.50 (d, J=6.6 Hz, 2H), 2.14 (m, 2H), 1.36 (m, 2H), 0.95 (m, 1H), 0.76 (d, J=6.7 Hz, 6H); IR (neat) 3068 (m), 3046(m), 2956(s), 2925 (m), 2864 (m), 1956 (w), 1886 (w), 1826(w), 1641 (s), 1471 (m), 1431(s), 1113 (s), 1000 (m), 910 (m), 743 (s), 702 (s) cm31 1 ; MS (FAB) m/e (rel. intensity) 323 (MH+, 15), 322 (24), 321 (89), 267, (17), 236 (36), 198 (20), 182 (63), 169 (100), 167 (15), 159 (31); HRMS (FAB) calcd forC21H25OSi: 321.1675 (MH+ -2), found: 321.1670.

Workup

  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 with hexane (50 mL)
  5. washThe combined organic extracts were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration to dryness in vacuo at rt

Sources & evidence

ORD record
ord-41d5d7fa2a614c559afe7344b6600928
Source dataset
uspto-grants-1998_06
Patent number
US05760019

Reaction notes

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