Water → HCID 67982825, compound

HRID 718528Notes

Reaction equation

HRID 718528 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][C:10]=1[O:24][CH2:25][CH3:26])(C)C)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH2:25]([O:24][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:14][C:9]=1[OH:8])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67982732HCID 67982732, compound

Product 1

HCID 67982825HCID 67982825, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl(2-ethoxy-4-(3-phenylprop-1-enyl)phenoxy)-dimethylsilane (3.12 g, 8.46 mmol, 1.0 equiv.), in THF (17 mL), n-Bu4NF (10.2 mL, 10.2 mmol, 1.2 equiv., 1.0 M in THF) was added, and the mixture was stirred at 25° C. for 1 h. After addition of H2O, the aqueous layer was extracted with MTBE (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 95:5) to yield 1.60 g (74%) of the title compound as a yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with MTBE (2×)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 95:5)

Sources & evidence

ORD record
ord-5a6ec16d3d6642db9522558b24b45c33
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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