Tetrabutylammonium Fluoride → Benzyl 4-(6-Hydroxynaphthalen-2-yl)but-3-ynylcarbamate

HRID 1644232Notes

Reaction equation

HRID 1644232 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]#[C:20][CH2:21][CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]#[C:20][CH2:21][CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57828221HCID 57828221, compound

Product 1

HCID 57828225Benzyl 4-(6-Hydroxynaphthalen-2-yl)but-3-ynylcarbamateYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 4-[6-(tert-butyldimethylsilyloxy)naphthalen-2-yl]but-3-ynylcarbamate (83, 2.5 g, 5.44 mmol) in anhydrous THF (25 mL) at 0° C. was added dropwise tetrabutylammonium fluoride (1 M in THF, 6.0 mL) and the mixture was stirred for 2 h at room temperature. The resulting solution was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 95:5 CH2Cl2/MeOH) to afford carbamate 84 (2.0 g, 50%) as a pale yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.82 (s, 1H), 7.67 (d, J=9.6 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.37-7.29 (m, 6H), 7.11-7.08 (m, 2H), 5.30 (br s, 2H), 5.14 (s, 2H), 3.48 (q, J=6.3 Hz, 2H), 2.68 (t, J=6.6 Hz, 2H).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, 95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-ae2b1763a37f4464b9d3e827fbae12ae
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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