Sodium Bicarbonate → HCID 54252927, compound

HRID 1275694Notes

Reaction equation

HRID 1275694 reaction equation
[CH3:1][O:2][CH:3]1[CH:8]2[CH:9]=[CH:10][CH2:11][CH:7]2[C:6]([CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][O:4]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:41](=O)(O)[O-:42].[Na+].CCCCCC.C(OC(=O)C)C>O1CCCC1>[OH:42][CH2:41][C:9]1[C@H:8]2[C@H:3]([O:2][CH3:1])[O:4][CH:5]=[C:6]([CH2:12][O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C@H:7]2[CH2:11][CH:10]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 86756118HCID 86756118, compound

Product 1

HCID 54252927HCID 54252927, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.578 g (3.53 mmol) of (1R,4aS,7aS)-7-t-butyldimethylsilyloxymethyl)-1-methoxy-4-(p-methoxybenzyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran was dissolved in 13 mg of tetrahydrofuran and then 3.8 ml (3.89 mmol) of tetrabutylammoniumfluoride (1M in THF) was added thereto. After stirring for 2 hours, the reaction was stopped by adding saturated aqueous sodium bicarbonate solution. 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=3/1, v/v) to obtain 0.821 g (Yield 70%) of (1R,4aS,7aS)-7-hydroxymethyl-1-methoxy-4-(p-methoxybenzyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran as a colorless oil.

Workup

  1. extractionThe reaction solution was extracted with diethylether and saturated saline solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-48176a5c8ae04fb2a775645481a63893
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

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