Tetrabutylammonium Fluoride → HCID 69082482, compound

HRID 1396290Notes

Reaction equation

HRID 1396290 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]([C:19]1[S:20][C@H:21]2[O:27][C@H:26]([CH2:28][O:29][Si](C(C)(C)C)(C)C)[C@@H:25]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[C@H:24]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=3)[C@H:22]2[N:23]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:14]([O:13][C:12](=[O:18])[N:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:19]1[S:20][C@H:21]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)[C@H:24]([O:47][CH2:48][C:49]3[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=3)[C@H:22]2[N:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69085336HCID 69085336, compound

Product 1

HCID 69082482HCID 69082482, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 133 (7.5 g, 9.3 mmol) in THF (30 mL) was treated with TBAF (4.9 g, 18.6 mmol) for 3 hours at room temperature. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 3%-10% ethyl acetate in petroleum ether to afford 134 as a light yellow syrup (5.8 g, 90%). (ES, m/z) [M+H]+ 695.0; 1H NMR (300 MHz, CDCl3) δ 7.21-7.36 (m, 9H), 6.80-6.85 (m, 4H), 6.09 (d, J=6.3 Hz, 1H), 4.50-4.55 (m, 4H), 4.49 (s, 2H), 4.31-4.33 (m, 1H), 4.05-4.06 (m, 1H), 3.84-3.91 (m, 1H), 3.82 (s, 3H), 3.83 (s, 3H), 3.56-3.67 (m, 2H), 3.30-3.53 (m, 5H), 1.56 (s, 9H).

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layer was washed with brine (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by a silica gel column
  8. washeluted with 3%-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-9c243d18125b454397c79513ca13ff99
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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