Sodium hydride → HCID 54164450, compound

HRID 1275693Notes

Reaction equation

HRID 1275693 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[C@H:16]2[C@H:17]([O:23][CH3:24])[O:18][CH:19]=[C:20]([CH2:21][OH:22])[C@H:15]2[CH2:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.CCCCCC.C(OC(=O)C)C>[Si:3]([O:10][CH2:11][C:12]1[C@H:16]2[C@H:17]([O:23][CH3:24])[O:18][CH:19]=[C:20]([CH2:21][O:22][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[C@H:15]2[CH2:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 516892Sodium BicarbonateHCID 54083493HCID 54083493, compound

Product 1

HCID 54164450HCID 54164450, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

0.402 g (10.04 mmol) of sodium hydride was introduced into a reaction vessel and 10ml of dried dimethylformanide was added thereto under nitrogen atmosphere. After the reaction temperature was lowered to 5° C., 3 g (8.37 mmol) of (1R,4aS,7aS)-7-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-1-methoxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran which is diluted in advance in 20 ml of dried dimethylfor- mamide was slowly added dropwise thereto. After stirring for one hour, 1.36 ml (10.04 mmol) of p-methoxybenzylchloride was added to the solution, which was then stirred for 6 hours while its temperature being slowly raised to room temperature. Saturated aqueous sodium bicarbonate solution was added to stop the reaction. The reaction solution was extracted with diethylether and saturated saline solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was subjected to silica gel column chromatography (eluent: n-hexane/ethylacetate=8/1, v/v) to obtain 1.578 g (Yield 42.2%) of (1R,4aS,7aS)-7-(t-butyldimethylsilyloxymethyl)-1-methoxy-4-(p-methoxybenzyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran as a colorless oil.

Workup

  1. addition10ml of dried dimethylformanide was added
  2. customwas lowered to 5° C.
  3. additionwas slowly added dropwise
  4. stirringwas then stirred for 6 hours while its temperature
  5. customthe reaction
  6. extractionThe reaction solution was extracted with diethylether and saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a3c7cf17d15c4cdaa1b27c8f201f8132
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

Loading…