Tetrabutylammonium Fluoride → HCID 86594478, compound

HRID 392915Notes

Reaction equation

HRID 392915 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27](=[O:48])[C:28]1[CH:33]=[C:32]([C:34]#[C:35][Si](C)(C)C)[CH:31]=[CH:30][C:29]=1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CCOCC>[CH2:19]([O:26][C:27](=[O:48])[C:28]1[CH:33]=[C:32]([C:34]#[CH:35])[CH:31]=[CH:30][C:29]=1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69705918HCID 69705918, compound

Product 1

HCID 86594478HCID 86594478, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetra-butyl ammonium fluoride (2.97 mL of a 1 M solution in THF, 2.97 mmol) was added to a solution of 2-benzyloxy-5-(2-trimethylsilyl-ethynyl)-benzoic acid benzyl ester (1.07 g, 2.58 mmol) in THF (10 mL) at room temperature. After 30 minutes, the mixture was diluted with ether (20 mL) and washed with water (3×30 mL) and brine (1×30 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (5% ethyl acetate/hexanes) to afford 687 mg (78%) product as a light orange oil. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 1H, J=2 Hz); 7.52 (dd, 1H, J=9.1, 1 Hz); 7.38 (m, 10H); 6.95 (d, 1H, J=9.1 Hz); 5.35 (s, 2H); 5.19 (s, 2H); 3.0 (s, 1H).

Workup

  1. washwashed with water (3×30 mL) and brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-29784869b76a46aca4b97e4d38062220
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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