Sodium hydride → HCID 54364393, compound

HRID 344928Notes

Reaction equation

HRID 344928 reaction equation
[CH2:1]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:20])=[C:8]([C:10]2[CH:11]=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:13]=[CH:14][C:15]=2[OH:16])[CH:9]=1.[H-].[Na+].[H][H].I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][O:38]1>CN(C=O)C>[CH2:3]([C:4]1[CH:5]=[CH:6][C:7]([OH:20])=[C:8]([C:10]2[CH:11]=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:13]=[CH:14][C:15]=2[O:16][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][O:38]2)[CH:9]=1)[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 72300MagnololHCID 13671960HCID 13671960, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54364393HCID 54364393, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution was prepared by dissolving 0.53 g of Magnolol into DMF. The solution, wherein 80 mg of sodium hydride (60% oiliness) was added, was stirred at room temperature until generation of hydrogen gas stopped. The reaction mixture, added 1.0 g of 2-(10-iododecyloxy)tetrahydropyrane, was heated to 70° C. with stirring for 3 hours. The solvent in the reaction mixtures was removed under reduced pressure, and an aqueous solution of ammonium chloride was added into the residue to extract with diethylether. The extract was washed with an aqueous solution saturated with NaCl, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=10:1) to yield 0.27 g of 4-allyl-2-[5-allyl-2-(10-tetrahydropyranyloxydecyloxy)phenyl]phenol. The subject thus obtained was dissolved into 10 ml of ethanol, 1 ml of hydrochloric acid was added thereinto and stirred for 3 hours at room temperature. The reactant, wherein 100 ml of water was added, was extracted with diethylether. The extract was washed with water, sodium hydrogencarbonate and an aqueous solution saturated with NaCl in turn, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=15:1) to yield 0.16 g of 4-allyl-2-[5-allyl-2-(10-hydroxy-decyloxy)phenyl]phenol.

Workup

  1. customA solution was prepared
  2. customThe solvent in the reaction mixtures
  3. customwas removed under reduced pressure
  4. additionan aqueous solution of ammonium chloride was added into the residue
  5. extractionto extract with diethylether
  6. washThe extract was washed with an aqueous solution saturated with NaCl
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2396d8ac13864feda4f9ea197416a23f
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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