Tetrabutylammonium Fluoride → HCID 69084598, compound

HRID 1396298Notes

Reaction equation

HRID 1396298 reaction equation
[CH2:1]([N:4]([C:12]1[S:13][C@H:14]2[O:20][C@H:19]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[C@@H:18]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C@H:17]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=3)[C@H:15]2[N:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:4]([C:12]1[S:13][C@H:14]2[O:20][C@H:19]([CH2:21][OH:22])[C@@H:18]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[C@H:17]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=3)[C@H:15]2[N:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69082413HCID 69082413, compound

Product 1

HCID 69084598HCID 69084598, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 147 (15 g, 21 mmol) in THF (100 mL) was treated with TBAF (8.4 g, 32 mmol) for 3 hours at room temperature. The reaction was quenched with water (150 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (2×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash column chromatography with 10%-30% ethyl acetate in petroleum ether to afford 148 as a light yellow syrup (11.3 g, 90%). (ES, m/z): [M+H]+ 601.0; 1H NMR (300 MHz, CDCl3) δ 7.36-7.33 (m, 2H), 7.21-7.19 (m, 2H), 6.91-6.82 (m, 4H), 6.09 (d, J=6.6 Hz, 1H), 5.92-5.80 (m, 1H), 5.19-5.00 (m, 2H), 4.70-4.58 (m, 2H), 4.55-4.36 (m, 4H), 4.32-4.24 (m, 2H), 3.82 (s, 3H), 3.83 (s, 3H), 3.75-3.68 (m, 2H), 3.64-3.52 (m, 2H), 1.56 (s, 9H).

Workup

  1. customThe reaction was quenched with water (150 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layer was washed with brine (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography with 10%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-fb8dd2ed44444bd3abaec9289a029398
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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