Ethyl acetate hexane → HCID 86743009, compound

HRID 1761784Notes

Reaction equation

HRID 1761784 reaction equation
[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][CH:7]([C:21]([CH3:23])=[CH2:22])[CH2:8][CH2:9]/[C:10](/[CH3:20])=[CH:11]/[CH2:12][CH2:13][C:14]([CH3:19])=[CH:15][CH:16]([OH:18])[CH3:17])([CH3:4])([CH3:3])[CH3:2].CCCCCC.C(OCC)(=O)C>ClCCl.[O-2].[O-2].[Mn+4]>[C:1]([Si:5]([CH3:24])([CH3:25])[O:6][CH:7]([C:21]([CH3:23])=[CH2:22])[CH2:8][CH2:9]/[C:10](/[CH3:20])=[CH:11]/[CH2:12][CH2:13][C:14]([CH3:19])=[CH:15][C:16](=[O:18])[CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 86743010HCID 86743010, compound

Product 1

HCID 86743009HCID 86743009, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

5 g of (7E)-11-(tert.-butyldimethylsiloxy)-4,8,12-trimethyl-3,7,12-tridecatrien-2-ol are added dropwise at 0° to a suspension of 25 g of manganese dioxide (active, precipitated) in 50 ml of dichloromethane. After stirring at room temperature for 5 hours the reaction mixture is filtered over sodium sulphate and the filtrate is evaporated. The material obtained is subjected twice more to the same oxidation process with fresh manganese dioxide each time in order to achieve complete reaction. Chromatography of the crude product obtained on silica gel with hexane-ethyl acetate 2%→5% yields (7E)-11-(tert.-butyldimethylsiloxy)-4,8,12-trimethyl-3,7,12-tridecatrien-2-one as a yellowish which has a purity of 95% in accordance with a gas chromatography. NMR (250 MHz, CDCl3): 6.05 (s, H-C(3)); 5.1 (m, H-C(7)); 4.84 and 4.75 (2m, 2H-C(13)); 4.0 (t, J=6.5, H-C(11)); 2.3-1.4 (m, 4CH2, 3CH 3); 0.89 (s, SiC(CH3)3); 0.35 and 0.0 (2s, Si(CH3)2).

Workup

  1. filtrationis filtered over sodium sulphate
  2. customthe filtrate is evaporated
  3. customThe material obtained
  4. customreaction

Sources & evidence

ORD record
ord-7a4302c2f80c45989fc4b9342d19e123
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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