Water → HCID 86743005, compound

HRID 1761781Notes

Reaction equation

HRID 1761781 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][CH:7]([C:24]([CH3:26])=[CH2:25])[CH2:8][CH2:9]/[C:10](/[CH3:23])=[CH:11]/[CH2:12][CH2:13][C:14]([CH3:22])=[CH:15][C:16](OC(C)C)=[O:17])([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+].O.S(=O)(=O)(O)O>CCCCCC>[C:1]([Si:5]([CH3:27])([CH3:28])[O:6][CH:7]([C:24]([CH3:26])=[CH2:25])[CH2:8][CH2:9]/[C:10](/[CH3:23])=[CH:11]/[CH2:12][CH2:13][C:14]([CH3:22])=[CH:15][CH2:16][OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 16684438Red-AlHCID 86743006HCID 86743006, compound

Product 1

HCID 86743005HCID 86743005, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

24.5 ml of sodium dihydro-bis(2-methoxyethoxy)-aluminate (70% solution in toluene, "Vitride") are slowly added dropwise at 0° to a solution of 32.6 g of isopropyl (6E)-10-(tert.-butyldimethylsiloxy)-3,7,11-trimethyl-2,6,11-dodecatrienoate in 80 ml of hexane. After stirring at room temperature for 2 hours a further 2.5 ml of "Vitride" are added dropwise. The reaction mixture is stirred for a further hour and then treated cautiously with 20 ml of water, whereupon the mixture is poured into ice-water. After adding 70 ml of 50% sulphuric acid the mixture is extracted twice with hexane. The combined extracts are washed with 2N sulphuric acid, water, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated. The residue is chromatographed on silica gel with hexane-ethyl acetate-triethylamine 80:20:0.1, whereby (6E)-10-(tert.-butyldimethylsiloxy)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol is obtained as a colourless oil. NMR (80 MHz, CDCl3); 5.45 (t, J=7.1 olefin. H); 5.15 (m, 1 olefin. H); 4.95-4.75 (m, 2H-C(12)); 4.2 (d, J=7, 2H-C(1)); 4.05 (t, J=6.5, H-C(10)); 2.2-1.3 (m, 4CH2, 3CH3); 0.9 (s, SiC(CH3)3); 0.05 and 0.0 (2s, Si(CH3)2).

Workup

  1. additionare added dropwise
  2. extractionis extracted twice with hexane
  3. washThe combined extracts are washed with 2N sulphuric acid, water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with hexane-ethyl acetate-triethylamine 80:20:0.1

Sources & evidence

ORD record
ord-7356e1ce1f3e4b2a9ac2485251e158a1
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

Loading…