Ethyl ketone → 4-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol

HRID 546807Notes

Reaction equation

HRID 546807 reaction equation
C([Li])CCC.CCCCCC.[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH3:33])[CH:27]=1)([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[C:19]([CH3:25])[CH:18]=1)[CH2:15][CH3:16])[CH3:13].[CH3:34][CH2:35][C:36](=[O:39])[CH2:37][CH3:38]>O1CCCC1>[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH3:33])[CH:27]=1)([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:36]([CH2:37][CH3:38])([OH:39])[CH2:35][CH3:34])=[C:19]([CH3:25])[CH:18]=1)[CH2:15][CH3:16])[CH3:13]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 8058HexaneHCID 585982954-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenolHCID 178418339Butyllithium

Product 1

HCID 574329954-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl)-propyl}-2-methyl-phenolYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.5 M solution of n-butyllithium in hexane (14.7 mL, 36.73 mmol) was added to a solution of 4-[1-ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(3); 4.28 g, 14.69 mmol) in tetrahydrofuran (92 mL) at −78° C. Pentan-3-one (4.85 mL, 44.07 mmol) was added to the mixture at −78° C., and the mixture was stirred at the same temperature for three hours and concentrated under reduced pressure. Ethyl acetate and water were added to the residue, and a 1 N hydrochloric acid aqueous solution was added to adjust the pH to about 7. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=6/1) to give the title compound (3.66 g, 62%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate and water were added to the residue
  3. additiona 1 N hydrochloric acid aqueous solution was added
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-e3c0d944ea89458797fd9400e092810a
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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