Tetrabutylammonium Fluoride → HCID 58968721, compound

HRID 2075098Notes

Reaction equation

HRID 2075098 reaction equation
[CH3:1][O:2][C:3]1([C:9]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:10]=2[CH2:11][O:12][Si](C(C)(C)C)(C)C)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1([C:9]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:20][C:10]=2[CH2:11][OH:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58968732HCID 58968732, compound

Product 1

HCID 58968721HCID 58968721, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-(1-methoxycyclohexyl)-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane (61 mg, 0.15 mmol) and tetrabutylammonium fluoride (0.2 mL; 0.2 mmol; 1.0M in tetrahydrofuran) was stirred in tetrahydrofuran (1 mL). The reaction was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure. The residue was purified by 4 g RediSep column (Teledyne Isco inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane) to give 30 mg (69% yield) of a colorless gum. MS-GC (El): Calc: 288.3, Found: 288 (M). 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (s, 1H), 7.50 (d, J=8.30 Hz, 1H), 7.41 (d, J=8.30 Hz, 1H), 5.03 (s, 2H), 2.99 (s, 3H), 2.24 (d, J=13.28 Hz, 2H), 1.8-1.57 (m, 7H), 1.28 (m, 1H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by 4 g RediSep column (Teledyne Isco inc., Lincoln Nebr.) (eluted with 10-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c144ada8ecb94eef86cc98bed4462cc7
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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