Potassium Chloride → HCID 90358076, compound

HRID 522177Notes

Reaction equation

HRID 522177 reaction equation
[Hg:1](OC(C)=O)OC(C)=O.[CH2:10]([O:17][CH2:18][C@@H:19]([OH:49])[C@@H:20]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@H:21]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:22]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:23]=[CH2:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-:50].[K+]>C1COCC1.CCOC(C)=O>[CH2:26]([O:25][C@H:22]1[C@@H:21]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:20]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:19]([CH2:18][O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:49][C@@H:23]1[CH2:24][Hg:1][Cl:50])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 4873Potassium ChlorideHCID 11753025HCID 11753025, compoundHCID 16683746Diacetyloxymercury

Product 1

HCID 90358076HCID 90358076, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Hg(OAc)2 (0.88 g, 2.8 mmol, 1.0 equiv) in dry THF (50 mL) under nitrogen atmosphere was added (2R,3R,4R,5R)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol (1.5 g, 2.78 mmol, 1.0 equiv) dissolved in 20 mL of dry THF. The reaction was stirred at room temperature for 16 hours and then a saturated aqueous solution of potassium chloride (0.50 g, 4.5 mmol, 1.6 equiv) was added. After 30 minutes, the reaction mixture was diluted with EtOAc (80 mL), washed with water (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material thus obtained was purified by silica gel chromatography, eluting with 30% EtOAc in petroleum ether, to give (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride as a pale yellow oil (1.5 g, 72%). 1H NMR (300 MHz, CDCl3) δ 7.45-7.15 (m, 20H), 4.62-4.39 (m, 7H), 4.33 (d, J=11.9 Hz, 1H), 4.24-4.11 (m, 1H), 4.08 (ddd, J=7.7, 5.9, 2.2 Hz, 1H), 3.89-3.76 (m, 2H), 3.72 (dd, J=4.2, 2.3 Hz, 1H), 3.68-3.57 (m, 1H), 3.39 (dd, J=8.5, 2.9 Hz, 1H), 2.18-1.96 (m, 2H). ESI (M+H2O) 792.0; calc for C35H37ClHgO5 774.2.

Workup

  1. waitAfter 30 minutes
  2. washwashed with water (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material thus obtained
  7. customwas purified by silica gel chromatography
  8. washeluting with 30% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-8b079930b27b4eedbb743a16ccda4ce2
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

Loading…