Ethyl Acetate → 2-(3-(4-bromo-2-(trifluoromethyl)phenoxy)propoxy)tetrahydro-2H-pyran

HRID 2079528Notes

Reaction equation

HRID 2079528 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.O.[C:18]1(C)C=[CH:22][C:21](S(O)(=O)=O)=[CH:20][CH:19]=1.C(OCC)(=[O:31])C>C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][CH:22]2[CH2:21][CH2:20][CH2:19][CH2:18][O:31]2)=[C:4]([C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 576575913-(4-Bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol

Product 1

HCID 576575642-(3-(4-bromo-2-(trifluoromethyl)phenoxy)propoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 3-(4-bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol (12 g), 3,4-dihydro-2H-puran (6.75 g) and p-toluenesulfonic acid hydrate (0.76 g) in THF (100 ml) was stirred at room temperature for 1 hour then diluted with 10% sodium carbonate (50 ml) and extrated with ethyl acetate (2×150 ml). Organic layer was then dried over sodium sulphate, solvent removed under reduced pressure to give expected product (15 g).

Workup

  1. dry with materialOrganic layer was then dried over sodium sulphate, solvent
  2. customremoved under reduced pressure

Sources & evidence

ORD record
ord-265484f509b847db9ab02dee04ada42b
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

Loading…