HCID 86743005, compound → HCID 86743007, compound

HRID 1761782Notes

Reaction equation

HRID 1761782 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][CH2:16][OH:17])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[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]/[CH2:12][CH2:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86743005HCID 86743005, compound

Product 1

HCID 86743007HCID 86743007, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

10.58 g of (6E)-10-(tert.-butyldimethylsiloxy)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol are added dropwise at 0° to a suspension of 110 g of manganese dioxide (precipitated, active) in 220 ml of dichloromethane and the mixture is stirred at room temperature for 2 hours. After filtration over Hyflo the filtrate is concentrated and oily residue is chromatographed on silica gel with hexane-ethyl acetate-triethylamine 90:10:0.1. There is obtained (6E)-10-(tert.-butyldimethylsiloxy)-3,7,11-trimethyl-2,6,11-dodecatrienal as a yellowish oil. NMR (80 MHz, CDCl3): 10.1 (d, J=8, H-C(1)); 6.0 (d, J=8, H-C(2)); 5.2 (m, H-C(6)); 5.0-4.8 (m, 2H-C(12)); 4.1 (t, J=6.5, H-C(10)); 2.4-1.4 (m, 4CH2, 3CH3); 0.95 (s, SiC(CH3)3); 0.1 and 0.05 (2s, Si(CH3)2).

Workup

  1. filtrationAfter filtration over Hyflo the filtrate
  2. concentrationis concentrated
  3. customoily residue is chromatographed on silica gel with hexane-ethyl acetate-triethylamine 90:10:0.1

Sources & evidence

ORD record
ord-b796d8e5831042a6a5d05632706dbe20
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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