Water → 4-[4-(4-Ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene

HRID 846461Notes

Reaction equation

HRID 846461 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[CH:17])=[CH:11][CH:10]=1)[CH3:7].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][C:22]=1[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CCCCCC.O1CCCC1.ClCCl>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][CH2:17][CH2:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:6][CH3:7])=[CH:10][CH:11]=2)([CH3:18])[CH3:19])=[CH:23][C:22]=1[O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 13505141HCID 13505141, compoundHCID 178418339Butyllithium

Product 1

HCID 1191504-[4-(4-Ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzeneYield 76.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

0.01 mol of a solution of butyllithium in hexane is added at -30° C. with stirring to 1.9 g (0.01 mol) of 3-[p-ethoxyphenyl]-3-methyl-1-butine in 10 ml of absolute tetrahydrofuran. After stirring for 3 hours, a solution of 2.2 g (0.01 mol) of 4-fluoro-3-phenoxy-benzaldehyde in 10 ml of tetrahydrofuran is added to the reaction mixture. The reaction mixture is warmed to room temperature and, after stirring at this temperature for 5 hours, water and dichloromethane (100 ml each) are added. The organic phase is separated off and concentrated in vacuo. 3.6 g of crude product are obtained, which contains 85% of 1-[4-fluoro-3-phenoxy-phenyl]-4-[p-ethoxyphenyl]-4-methyl-pent-1-in-1-ol (in addition to 7% of the corresponding ketone) according to GC-MS analysis. The crude product is catalytically hydrogenated under the conditions described in Example 8 δ). 3 g of 1-[4-fluoro-3-phenoxy-phenyl]-4-[p-ethoxyphenyl]-4-methyl-pentane (89% pure according to GC-MS analysis=2.7 g=69% of theory) are obtained. The compound is obtained pure by chromatography on silica gel (nD20 : 1.5580).

Workup

  1. stirringafter stirring at this temperature for 5 hours
  2. customThe organic phase is separated off
  3. concentrationconcentrated in vacuo
  4. custom3.6 g of crude product are obtained

Sources & evidence

ORD record
ord-951cb190368a4b48aad98230111e4186
Source dataset
uspto-grants-1992_08
Patent number
US05136114

Reaction notes

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