Sodium hydride → HCID 14421669, compound

HRID 2292216Notes

Reaction equation

HRID 2292216 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:13].[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30].C(OCC)C.O>CN(C)C=O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH:5]=[CH:4][C:3]=1[C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])[O:11][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 810936-BromohexanenitrileHCID 14421654HCID 14421654, compoundHCID 21584184Diethylether water

Product 1

HCID 14421669HCID 14421669, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 12.5 g of (2,4-dihydroxy-3-propylphenyl)(2-hydroxyphenyl)methanone in 460 ml of dimethylformamide were added 1.83 g of 60% sodium hydride in oil. The mixture was stirred for one hour under a nitrogen atmosphere. A solution of 4.9 ml of 6-bromohexanenitrile in a small volume of dimethylformamide was added. The reaction was stirred at 60° C. overnight, cooled to 25° C., and poured into a diethyl ether/water mixture. The layers were separated, and the organic layer was washed three times with water, dried over magnesium sulfate, filtered, and evaporated. Purification by high pressure liquid chromatography over silica gel eluting with a 15-35% ethyl acetate/hexane gradient, and evaporation of the desired fractions provided 6.1 g of the desired title product. Crystallization from ethyl acetate/hexane provided material with a melting point of 62°-63° C.

Workup

  1. stirringThe reaction was stirred at 60° C. overnight
  2. customThe layers were separated
  3. washthe organic layer was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by high pressure liquid chromatography over silica gel eluting
  8. customwith a 15-35% ethyl acetate/hexane gradient, and evaporation of the desired fractions

Sources & evidence

ORD record
ord-f391d48871cf4405ad6543dba26e2d22
Source dataset
uspto-grants-1989_01
Patent number
US04801616

Reaction notes

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