Tetrabutylammonium Fluoride → HCID 21087722, compound

HRID 1272395Notes

Reaction equation

HRID 1272395 reaction equation
CC(C)(C)[Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:27][CH2:28][CH2:29][S:30][S:31][CH2:32][CH2:33][NH:34][C:35](=[O:74])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][Si](C1C=CC=CC=1)(C1C=CC=CC=1)C(C)(C)C)=[O:26].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:56][CH2:55][CH2:54][O:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][C:35]([NH:34][CH2:33][CH2:32][S:31][S:30][CH2:29][CH2:28][NH:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][OH:4])=[O:74]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58803876HCID 58803876, compound

Product 1

HCID 21087722HCID 21087722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 30 (1.76 g, 1.40 mmol) was dissolved in tetrahydrofuran (50 mL) and terabutylammonium fluoride in tetrahydrofuran (1.0 M, 2.95 mL) was added. The solution was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo. The resulting oil was dissolved in dichloromethane (200 mL) and the solution was washed with aqueous hydrochloric acid (1 N, 100 mL), water (75 mL) and brine (75 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The crude product was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe resulting oil was dissolved in dichloromethane (200 mL)
  3. washthe solution was washed with aqueous hydrochloric acid (1 N, 100 mL), water (75 mL) and brine (75 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-233d4af713ef4250b8cd32da35ed4d06
Source dataset
uspto-grants-2007_04
Patent number
US07208322B2

Reaction notes

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