Tetrabutylammonium Fluoride → HCID 68815428, compound

HRID 733295Notes

Reaction equation

HRID 733295 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:38])[CH:16]([CH3:37])[C:17](=[O:36])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][Si](C(C)(C)C)(C)C)=[C:22]([O:34][CH3:35])[CH:21]=2)=[CH:11][C:10]=1[O:39][CH3:40])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:38])[CH:16]([CH3:37])[C:17](=[O:36])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:34][CH3:35])[CH:21]=2)=[CH:11][C:10]=1[O:39][CH3:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68816082HCID 68816082, compound

Product 1

HCID 68815428HCID 68815428, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,5-Bis(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-2-methyl-pentane-1,3-dione (250 mg, 0.43 mmol) was dissolved in anhydrous THF (8 ml) and stirred at room temperature under a nitrogen atmosphere. Tetrabutylammonium fluoride (0.27 ml, 0.94 mmol) was added and the mixture was stirred for 2 h and monitored by TLC. After this time the solvents were removed under vacuum to leave a residue which was purified on silica gel column using dichloromethane/ethyl acetate (1:0 to 5:1) to give 1,5-bis(4-hydroxy-3-methoxyphenyl)-2-methylpentane-1,3-dione (102 mg, 67%) as a light green oil: LCMS (m/z) 359 (M+H)+, 381 (M+Na)+; 1H NMR (400 MHz, CDCl3) δ 1.40 (3H, d, J=7.2 Hz, CH3), 2.63-2.82 (4H, m, 2×CH2), 3.81 (3H, s, OCH3), 3.94 (3H, s, OCH3), 4.39 (1H, q, J=7.2 Hz, H-2), 5.45 (1H, brs, OH), 6.13 (1H, brs, OH), 6.58-6.60 (2H, m, 2×ArH), 6.76 (1H, d, J=8.4 Hz, ArH), 6.92 (1H, d, J=8.4 Hz, ArH), 7.44-7.48 (2H, m, 2×ArH) ppm; 13C NMR (100 MHz, CDCl3) δ 13.57, 29.34, 42.17, 55.73, 55.97, 56.13, 110.31, 110.97, 113.98, 114.20, 120.77, 124.08, 128.80, 132.57, 143.81, 146.27, 146.80, 150.95, 195.57, 206.67 ppm.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. customAfter this time the solvents were removed under vacuum
  3. customto leave a residue which
  4. customwas purified on silica gel column

Sources & evidence

ORD record
ord-4d61a33b05c840558e0ae608bbc82f0a
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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