Potassium Chloride → HCID 14158192, compound

HRID 522181Notes

Reaction equation

HRID 522181 reaction equation
[Hg:1](OC(C)=O)OC(C)=O.[CH2:10]([O:17][CH2:18][C@@H:19]([OH:42])[C@@H:20]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:21]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:22]([OH:25])[CH:23]=[CH2:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-:43].[K+]>C1COCC1.O.CCOC(C)=O>[CH2:27]([O:26][C@H:21]1[C@H:20]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@@H:19]([CH2:18][O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:42][C@H:23]([CH2:24][Hg:1][Cl:43])[C@@H:22]1[OH:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 4873Potassium ChlorideHCID 10694773HCID 10694773, compoundHCID 16683746Diacetyloxymercury

Product 1

HCID 14158192HCID 14158192, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Hg(OAc)2 (12.4 g, 38.8 mmol, 1.0 equiv) in dry THF (174 mL), under nitrogen, was added a solution of (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol (17.4 g, 38.8 mmol, 1.0 equiv) in dry THF (87 mL). The reaction mixture was stirred at room temperature for 16 hours and then a solution of KCl (4.3 g, 58.2 mmol, 1.5 equiv) in water (20 mL) was added. After 30 minutes, the reaction mixture was diluted with EtOAc (150 mL) and then washed with water (2×100 mL). The organic phase was then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give an oil. This oil was purified by silica gel chromatography, eluting with 20% EtOAc in hexane, to give (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride as a pale yellow oil (22.6 g, 85%). 1H NMR (400 MHz, CDCl3) δ 7.37-7.29 (m, 11H), 7.27-7.24 (m, 2H), 7.23-7.19 (m, 2H), 4.62-4.48 (m, 6H), 4.37 (dd, J=7.1, 3.7 Hz, 1H), 4.15 (dt, J=6.3, 4.1 Hz, 1H), 3.82 (dd, J=10.1, 6.7 Hz, 1H), 3.72 (q, J=2.8, 1.9 Hz, 1H), 3.65-3.59 (m, 2H), 3.53-3.47 (m, 2H), 2.06-2.00 (m, 1H), 1.77 (dd, J=12.1, 3.8 Hz, 1H). ESI (M+1-Cl) 647.1; calc for C28H31ClHgO5 684.2.

Workup

  1. waitAfter 30 minutes
  2. washwashed with water (2×100 mL)
  3. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThis oil was purified by silica gel chromatography
  8. washeluting with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-0814fe63adb340e7b41fe49c7d95ec7a
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

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