Tetrabutylammonium Fluoride → HCID 68815469, compound

HRID 733294Notes

Reaction equation

HRID 733294 reaction equation
[CH2:1]([CH:8]([C:17](=[O:36])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26][Si](C(C)(C)C)(C)C)=[C:22]([O:34][CH3:35])[CH:21]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([CH:8]([C:17](=[O:36])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:34][CH3:35])[CH:21]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68815521HCID 68815521, compound

Product 1

HCID 68815469HCID 68815469, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-2-Benzyl-5-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione (204 mg, 0.41 mmol) was dissolved in anhydrous THF (5 ml) and stirred at room temperature under a nitrogen atmosphere. TBAF (0.14 ml, 0.49 mmol) was added (yellow/green solution goes deep red colour) and the mixture was stirred overnight at room temperature. After this time the solvents were removed in vacuo to leave a residue which was purified on silica gel column using dichloromethane/diethyl ether (1:0 to 10:1) to give (E)-2-benzyl-5-(4-hydroxy-3-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione (134 mg, 85%) as a light green foam: 1H NMR (400 MHz, CDCl3) δ 3.34 (1H, dd, J=14.0, 7.2 Hz, CH2), 3.50 (1H, dd, J=14.0, 7.2 Hz, CH2), 3.92 (3H, s, OCH3), 4.95 (1H, t, J=7.2 Hz, H-2), 5.96 (1H, brs, OH), 6.68 (1H, d, J=16.0 Hz, H-4), 6.90 (1H, d, J=8.0 Hz, H-5′), 6.95 (1H, d, J=2.0 Hz, H-2′), 7.04 (1H, dd, J=8.0, 2.0 Hz, H-6′), 7.16-7.28 (5H, m, 5×ArH), 7.44 (2H, brt, J=8.0 Hz, 2×H-5″, H-3″, H-6), 7.53 (1H, d, J=16.0 Hz, H-5), 7.52-7.57 (1H, m, H-4″), 7.96-7.98 (2H, m, H-2″, H-6″) ppm.

Workup

  1. stirringwas stirred overnight at room temperature
  2. customAfter this time the solvents were removed in vacuo
  3. customto leave a residue which
  4. customwas purified on silica gel column

Sources & evidence

ORD record
ord-e6ab07de1bf745c4866b602c8107b315
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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