Tetrabutylammonium Fluoride → HCID 57828216, compound

HRID 1644217Notes

Reaction equation

HRID 1644217 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57828239HCID 57828239, compound

Product 1

HCID 57828216HCID 57828216, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1 M in THF, 1.0 mL) was added to a solution of benzyl 4-[4-(tert-butyldimethylsilyloxy)naphthalen-1-yl]butylcarbamate (19, 380 mg, 0.80 mmol) in anhydrous THF (15 ml) at room temperature. The reaction mixture was stirred for 2 h and concentrated to dryness. The residue was purified by column chromatography (silica gel, 3:1 hexanes/EtOAc) to afford butylcarbamate 20 (287 mg, 99%) as white solid: 1H NMR (300 MHz, CDCl3) δ 8.23-8.21 (m, 1H), 7.84-7.81 (m, 1H), 7.42-7.34 (m, 2H), 7.25-7.15 (m, 5H), 6.96 (d, J=7.5 Hz, 1H), 6.62 (d, J=7.5 Hz, 1H), 5.00 (br s, 2H), 4.65 (br s, 1H), 3.13 (q, J=6.6 Hz, 2H), 2.87 (t, J=7.5 Hz, 2H), 1.64-1.47 (m, 4H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by column chromatography (silica gel, 3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0f04c3dd59004cadb9c9c35c0a57e715
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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