Trifluoroacetic acid → HCID 86653779, compound

HRID 1021206Notes

Reaction equation

HRID 1021206 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH:26](O)[CH2:27][CH:28]=[CH2:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH:28]=[CH2:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86653778HCID 86653778, compound

Product 1

HCID 86653779HCID 86653779, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,5-Bis(benzyloxy)-3,4,6-trimethylphenyl)but-3-en-1-ol (3.7 g, 9.4 mmol) was dissolved into 10 mL CH2Cl2 and treated with Et3SiH (12 mL, 94.4 mmol.). To this clear, colorless solution was added trifluoroacetic acid (TFA) (10.5 mL, 142 mmol) neat over 3 minutes which darkened the solution and exothermed. The reaction vessel was placed in a room temperature water bath and let stir for 1.25 h. The reaction was concentrated to yellow oil via rotary evaporation and the residue dissolved in 100 mL methyl t-butyl ether (MTBE). To this was added 50 mL 2.5 M K2CO3, the layers separated and the aqueous phase extracted 3×50 mL MTBE. The combined organics were washed with 50 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to give 1-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-3-butene, (3.6 g) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ=7.51 (d, 4 H), 7.44-7.35 (m, 6 H), 5.90 (m, 1 H), 5.06 (d, 1 H), 4.97 (d, 1 H), 4.78 (s, 2 H), 4.74 (s, 2 H), 2.74 (m, 2 H), 2.27-2.24 (m, 9 H) ppm.

Workup

  1. customwas placed in a room temperature
  2. concentrationThe reaction was concentrated to yellow oil via rotary evaporation
  3. dissolutionthe residue dissolved in 100 mL methyl t-butyl ether (MTBE)
  4. additionTo this was added 50 mL 2.5 M K2CO3
  5. customthe layers separated
  6. extractionthe aqueous phase extracted 3×50 mL MTBE
  7. washThe combined organics were washed with 50 mL saturated aqueous NaCl
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-774251032b1548e69d2aa5045fb80272
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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