Methyl iodide → Methyl 6-[3-[tert-butylsilyloxy(diphenyl)methyl]phenyl]hexanoate

HRID 2117204Notes

Reaction equation

HRID 2117204 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:34](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.CCOCC>[CH3:34][O:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178455409HCID 178455409, compound

Product 1

HCID 131724102Methyl 6-[3-[tert-butylsilyloxy(diphenyl)methyl]phenyl]hexanoateYield 70.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-phenyl]-hexanoic acid (3.3 g, 7.2 mmol) in DMF (15 mL) is added potassium carbonate (1.09 g, 7.9 mmol) and iodomethane (500 μL, 7.9 mmol). The mixture is stirred for 6 hrs then diluted with ether. The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ether/hexanes) to give 2.42 g of title compound. 1H NMR (300 MHz, CDCl3) δ 7.70 (m, 4H), 7.38 (m, 6H), 7.20 (m, 2H), 7.12 (s, 1H), 7.06 (d, 1H), 4.76 (s, 2H), 3.65 (s, 3H), 2.59 (t, 2H), 2.30 (t, 2H), 1.64 (m, 4H), 1.37 (m, 2H), 1.10 (s, 9H).

Workup

  1. washThe organic layer is washed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography (eluting with 10% ether/hexanes)

Sources & evidence

ORD record
ord-7815940bd85145658acbb5d38ed7ef52
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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