Tetrabutylammonium Fluoride → HCID 12000037, compound

HRID 1910650Notes

Reaction equation

HRID 1910650 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:48]=[CH:49][C:50]=1[O:51][CH3:52])[CH2:6][O:7][CH2:8][C@@H:9]([O:22][CH2:23]/[CH:24]=[C:25](/[CH3:47])\[CH2:26][CH2:27]/[CH:28]=[CH:29]/[C:30]([CH3:46])([CH3:45])[CH2:31][CH2:32][C:33](=[CH2:44])[CH2:34]/[CH:35]=[C:36](\[CH3:43])/[CH2:37][CH2:38][CH:39]=[C:40]([CH3:42])[CH3:41])[CH2:10][O:11][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:48]=[CH:49][C:50]=1[O:51][CH3:52])[CH2:6][O:7][CH2:8][C@@H:9]([O:22][CH2:23]/[CH:24]=[C:25](/[CH3:47])\[CH2:26][CH2:27]/[CH:28]=[CH:29]/[C:30]([CH3:46])([CH3:45])[CH2:31][CH2:32][C:33](=[CH2:44])[CH2:34]/[CH:35]=[C:36](\[CH3:43])/[CH2:37][CH2:38][CH:39]=[C:40]([CH3:41])[CH3:42])[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67254613HCID 67254613, compound

Product 1

HCID 12000037HCID 12000037, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (R)-3-(3,4-dimethoxybenzyloxy)-1-triisopropylsiloxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-propane (8) (20.0 mg, 27.3 μmol, 1.00 eq.) in dry tetrahydrofuran (0.55 mL) was added 1 M tetrabutylammonium fluoride solution in tetrahydrofuran (41 μL, 40.9 μmol, 1.50 eq.) at 0° C. After being stirred at the same temperature for 1 h, the reaction mixture was poured into brine. The aqueous layer was extracted with two portions of ethyl acetate. The combined extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:ethyl acetate=55:45) to give (S)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-1-propanol (9) (15.4 mg, 26.4 μmol, 97%) as a colorless oil.

Workup

  1. extractionThe aqueous layer was extracted with two portions of ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=55:45)

Sources & evidence

ORD record
ord-180886a5ec76416e8fe75533ff66da82
Source dataset
uspto-grants-2013_12
Patent number
US08604004B2

Reaction notes

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