Toluene → HCID 46193183, compound

HRID 1293575Notes

Reaction equation

HRID 1293575 reaction equation
[C:1]([C@@H:4]([O:12][C:13](=[O:44])[CH2:14][C@H:15]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C:16]([CH3:35])([CH3:34])[C:17](=[O:33])[C@H:18]([CH3:32])[C@@H:19]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C@@H](C)C=C)[CH2:5]/[CH:6]=C(/C)\CC=C)(=[O:3])[CH3:2].[C:45]1([CH3:51])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[C:1]([C@H:4]1[O:12][C:13](=[O:44])[CH2:14][C@H:15]([O:36][Si:37]([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:39])[CH3:38])[C:16]([CH3:34])([CH3:35])[C:17](=[O:33])[C@H:18]([CH3:32])[C@@H:19]([O:24][Si:25]([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:26])[CH3:27])[C@@H:45]([CH3:51])[CH:50]=[CH:49][CH2:48][C:47]([CH3:46])=[CH:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 1140TolueneHCID 58733754HCID 58733754, compound

Product 1

HCID 46193183HCID 46193183, compound

Procedure

A solution of 50.0 mg (76.8 μmol) of (3S,6R,7S,8S)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-dec-9-enoic acid (Z)-(S)-1-acetyl-4-methyl-hepta-3,6-dienyl ester in 200 ml toluene was heated at reflux. 10.8 mg (11.5 μmol) of [RuCl2(PCy3)(ImH2Mes)(3-phenyl-indenylidene)] was added and the resulting yellowish solution stirred at reflux. After 30 min, a 50 ml sample was evaporated to dryness and to remove residual toluene, redissolved in 25 ml ethanol and evaporated to dryness to yield the title compound with 80% purity (HPLC method described in Example 4).

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. customa 50 ml sample was evaporated to dryness
  4. customto remove residual toluene
  5. dissolutionredissolved in 25 ml ethanol
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-164eeb3ae6e34738934e6b1ed19e4565
Source dataset
uspto-grants-2007_07
Patent number
US07238816B2

Reaction notes

Loading…