Potassium Carbonate → tert-Butyl 1,1,1,3,3,3-Hexafluoro-2-(4-vinylphenyl)-2-propyl Carbonate

HRID 1007059Notes

Reaction equation

HRID 1007059 reaction equation
[O:1](C(OC(C)(C)C)=O)[C:2]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=O.[F:16][C:17]([F:33])([F:32])[C:18]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[CH2:31])=[CH:26][CH:25]=1)([OH:23])[C:19]([F:22])([F:21])[F:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:2](=[O:1])([O:23][C:18]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[CH2:31])=[CH:26][CH:25]=1)([C:19]([F:21])([F:20])[F:22])[C:17]([F:32])([F:33])[F:16])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 27823772-(4-Ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 22667498tert-Butyl 1,1,1,3,3,3-Hexafluoro-2-(4-vinylphenyl)-2-propyl Carbonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared by a modification of the procedure of Przybilla, described in German Patent No. DE42072261A1 (Sep. 9, 1993), herein incorporated by reference. 9.35 mL of (t-BOC)2O (40.70 mmol) in THF (10 mL) was added to a mixture of 1,1,1,3,3,3-Hexafluoro-2-(4-vinylphenyl)-2-propanol (10.00 g, 37.01 mmol) and K2CO3 (10.00 g, 72.35 mmol) in THF (90 mL) was added. The reaction mixture was allowed to stir at room temperature for 4 days, concentrated, then partitioned between hexane/H2O. The aqueous solution was extracted with hexane, and the combined extracts were washed with brine, dried (Na2SO4), and concentrated to provide 15.17 g of a pale yellow oil. This material was purified by column chromatography on silica gel using 50:1 hexane/ethyl acetate to provide 5.16 g (38%) of a white solid, plus 4.68 g of a 90:10 mixture of protected/unprotected material; 1H NMR (CDCl3) δ 7.49 (d, 2ArH), 7.42 (d, 2ArH), 6.74 (dd, CH═), 5.83 (dd, ═CHH), 5.36 (dd, ═CHH), 1.49 (s, t-Bu).

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. custompartitioned between hexane/H2O
  4. extractionThe aqueous solution was extracted with hexane
  5. washthe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8727b7d5a7044f35b2a2e18d83070919
Source dataset
uspto-grants-2004_09
Patent number
US06794109B2

Reaction notes

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