Potassium Carbonate → HCID 178444581, compound

HRID 2050422Notes

Reaction equation

HRID 2050422 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[O:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:16][O:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:26][CH2:27][CH2:28][C@@H:29]([CH3:32])[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:32][C@@H:29]([CH2:30][CH3:31])[CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[O:15][CH2:16][C@H:17]([CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:18][O:19]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13800354(4S)-1-Bromo-4-methylhexaneHCID 19834830HCID 19834830, compound

Product 1

HCID 178444581HCID 178444581, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 0.9 g of 2-(4'-hydroxy-4-biphenylyl)-5-(4-pentenyl)-m-dioxane and 1.25 g of (S)-1-bromo-4-methylhexane in 25 ml of N,N-dimethylformamide was treated with 1.2 g of finely powdered potassium carbonate and the mixture was stirred overnight in an oil bath of 60° C. The suspension was suction filtered and the filtrate was concentrated in a vacuum. A solution of the residue in diethyl ether was washed twice with water, dried over sodium sulphate and concentrated. Chromatography of the crude product on 40 g of silica gel with hexane/ethyl acetate (vol. 23:2) and two-fold recrystallization from ethyl acetate gave pure (S)-trans-2-[4'-(4-methylhexyloxy)-4-biphenylyl]-5-(4-pentenyl)-m-dioxane; phase transition (S-S) 99.5° C., phase transition (S-SC *) 127° C., phase transition (SC *-Ch) 130° C., cl.p. (Ch-I) 148° C.

Workup

  1. filtrationsuction filtered
  2. concentrationthe filtrate was concentrated in a vacuum
  3. washA solution of the residue in diethyl ether was washed twice with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customChromatography of the crude product on 40 g of silica gel with hexane/ethyl acetate (vol. 23:2) and two-fold recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-34ae3d38dbe1483e88410b68602daf43
Source dataset
uspto-grants-1991_05
Patent number
US05013476

Reaction notes

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