tert-Butanol → 1-(Tert-butoxy)-3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol

HRID 705328Notes

Reaction equation

HRID 705328 reaction equation
[Cl:1][CH2:2][CH:3]([OH:26])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:25][O:24]3)=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.FC(F)(F)S([O-])(=O)=O.[Bi+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:57]([OH:61])([CH3:60])([CH3:59])[CH3:58]>>[C:57]([O:61][CH2:25][CH:23]([OH:24])[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:3]([OH:26])[CH2:2][Cl:1])=[CH:11][CH:10]=2)([CH3:14])[CH3:13])=[CH:16][CH:17]=1)([CH3:60])([CH3:59])[CH3:58]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 516892Sodium BicarbonateHCID 4169196Bisphenol A (3-chloro-2-hydroxypropyl)glycidyl etherHCID 9917655Bi(OTf)3

Product 1

HCID 1176899491-(Tert-butoxy)-3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-olYield 28%

Procedure

To a solution of racemic 1-chloro-3-(4-(2-(4-(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (300 mg, 0.8 mmol, 1 equiv) in t-Butanol (5 mL) was added solid Bismuth (III) trifluoromethanesulfonate (10 mg, 0.015 mmol, 1/50 equiv) in one portion and the mixture was stirred at room temperature for 12 h. Sodium bicarbonate was added (0.5 mL), the organic solvent was evaporated under reduced pressure, and the residue was extracted with dichloromethane (3×10 mL). The organic layer was washed with deionized water (2×10 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 40% to 80% ethyl acetate in hexane) to provide 1-(tert-butoxy)-3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (100 mg, 28%) as a foam.

Workup

  1. customthe organic solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (3×10 mL)
  3. washThe organic layer was washed with deionized water (2×10 mL)
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel (eluent: 40% to 80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4af76e2813ab42798820ef144bb527f0
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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