Methyl iodide → HCID 86743008, compound

HRID 1761783Notes

Reaction equation

HRID 1761783 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH:7]([C:20]([CH3:22])=[CH2:21])[CH2:8][CH2:9]/[C:10](/[CH3:19])=[CH:11]/[CH2:12][CH2:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Mg]I.[Mg].CI.[Cl-].[NH4+]>CCOCC>[C:1]([Si:5]([CH3:23])([CH3:24])[O:6][CH:7]([C:20]([CH3:22])=[CH2:21])[CH2:8][CH2:9]/[C:10](/[CH3:19])=[CH:11]/[CH:12]=[CH:13][C:14]([CH3:18])=[CH:15][C:16]([OH:17])=[CH2:25])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 86743007HCID 86743007, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 86743008HCID 86743008, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 7.3 g of (6E)-10-(tert.-butyldimethylsiloxy)-3,7,11-trimethyl-2,6,11-dodecatrienal in 10 ml of ether is added dropwise at -20° to a methylmagnesium iodide solution prepared from 0.56 g of magnesium shavings and 3.1 g of methyl iodide in 80 ml of ether. After stirring at -20° for 2 hours the reaction mixture is poured into a mixture of ice and saturated ammonium chloride solution and extracted twice with ether. The combined organic extracts are washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated. The oil which remains behind as the residue is chromatographed on silica gel with hexane-ethyl acetate-triethylamine 90:10:0.1, whereby (7E)-11-(tert.-butyldimethylsiloxy)-4,8,12-trimethyl-3,7,12-tridecadien-trien-2-ol is obtained as a colourless oil. NMR (250 MHz, CDCl3): 5.2 (d, J=8 H-C(3)); 5.1 (t, J=6.5, H-C(7)); 4.84 and 4.75 (2m, 2H-C(13)); 4.57 (m, H-C(2)); 4.0 (t, J=6.5, H-C(11)); 2.25-1.4 (m, 4CH2, 3CH3); 1.22 (d, J=6.5, 3H-C(1)); 0.89 (s, SiC(CH3)3); 0.04 and 0.0 (2s, Si(CH3)2).

Workup

  1. extractionextracted twice with ether
  2. washThe combined organic extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customis chromatographed on silica gel with hexane-ethyl acetate-triethylamine 90:10:0.1

Sources & evidence

ORD record
ord-16ebfbc5132c418da43f95ec9e601867
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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