Tetrabutylammonium Fluoride → HCID 59523103, compound

HRID 1424775Notes

Reaction equation

HRID 1424775 reaction equation
[CH2:1]([O:13][C:14]1[N:15]=[C:16]([Si](C(C)C)(C(C)C)C(C)C)[S:17][C:18]=1[C:19]1[S:23][C:22]([Si](C(C)C)(C(C)C)C(C)C)=[N:21][C:20]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:13][C:14]1[N:15]=[CH:16][S:17][C:18]=1[C:19]1[S:23][CH:22]=[N:21][C:20]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59523108HCID 59523108, compound

Product 1

HCID 59523103HCID 59523103, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6.0 g (7.06 mmol) of compound 12 in 150 mL of THF at 0° C. was added a solution of 21.2 mL (21.2 mmol) of tetrabutylammonium fluoride (1.0 M in THF) dropwise over 5 minutes. The mixture was stirred for 30 minutes at 0° C. then the ice bath was removed and the mixture was stirred at ambient temperature for 90 minutes. The mixture was treated with 2 mL of water, concentrated in vacuo, and separated by flash chromatography (silica gel, 5.5×35 cm, 1:1 hexane:chloroform to methylene chloride). The resulting solid was recrystallized from hexanes to give 2.98 g (79% yield) of compound 13 as colorless needles. 1H NMR (500 MHz) δ 8.43 (s, 2H), 4.47 (t, 4H, J=6.5 Hz), 1.90-1.20 (m, 40H), 0.90 (t, 6H, J=7.0 Hz).

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred at ambient temperature for 90 minutes
  3. additionThe mixture was treated with 2 mL of water
  4. concentrationconcentrated in vacuo
  5. customseparated by flash chromatography (silica gel, 5.5×35 cm, 1:1 hexane:chloroform to methylene chloride)
  6. customThe resulting solid was recrystallized from hexanes

Sources & evidence

ORD record
ord-7455a5d6d06d4bcdbf80ff4ade7fb002
Source dataset
uspto-grants-2015_01
Patent number
US08927971B2

Reaction notes

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