Sodium Hydroxide → HCID 14516971, compound

HRID 483722Notes

Reaction equation

HRID 483722 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([F:16])[CH:8]=1)([OH:6])[CH2:4][OH:5].[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[F:18][C:2]([F:1])([F:17])[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([F:16])[CH:8]=1)([OH:6])[CH2:4][O:5][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 13880760HCID 13880760, compound

Product 1

HCID 14516971HCID 14516971, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

1,1,1-Trifluoro-2-(3-fluoro-4-ethoxyphenyl)propan-2,3-diol (0.4 g), prepared as described in Example 8 (ii), 3-phenoxybenzyl bromide (0.39 g), 40% sodium hydroxide solution (5 cm3), dichloromethane (5 cm3) and tetra-n-butylammonium hydrogen sulphate (50 mg) were mixed, and stirred at room temperature under an atmosphere of nitrogen for 41/2 hours. The reaction mixture was partitioned between water and dichloromethane. The organic layer was separated and the aqueous layer washed with dichloromethane. The combined organic layers were dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure to give 1,1,1-trifluoro-2-(3-fluoro-4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propan-2-ol as an oil (0.67 g). The product was purified by column chromatography on a silica gel support, using n-hexane containing 15% by volume ethyl acetate as eluent.

Workup

  1. additionwere mixed
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with dichloromethane
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ba7011b87f564e018e8626e5f6b567ed
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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