Tetrabutylammonium Fluoride → HCID 21842609, compound

HRID 1737458Notes

Reaction equation

HRID 1737458 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:29][N:30]([CH3:40])[S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])(C(C)(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[OH:26][CH2:27][CH:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:29][N:30]([CH3:40])[S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21842650HCID 21842650, compound

Product 1

HCID 21842609HCID 21842609, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A THF solution of tetrabutylammonium fluoride (1.0 M, 3.9 mL, 3.9 mmol) was added to dropwise to a solution of N-(3-(tert-butyldimethylsilyloxy)-2-phenylpropyl)-N-methylbenzenesulfonamide (570 mg, 1.31 mmol) in 5.0 mL of THF. After stirring for 30 min at room temperature, the mixture was diluted with 50 mL of ethyl acetate and washed in sucession with 30 mL of 2.0 N aqueous HCl, 30 mL of saturated aqueous sodium bicarbonate, and 30 mL of brine. The organic layer was dried over sodium sulfate, decanted and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with 20-30% of ethyl acetate in hexanes to give 393 mg of the title compound as a colorless syrup. 1NMR (400 MHz, CD3OD): δ 7.74 (d, 2H, J=7 Hz), 7.64 (tt, 1H, J=7, 1 Hz), 7.56 (t, 2H, J=7 Hz), 7.33-7.20 (m, 5H), 3.79-3.71 (m, 2H), 3.41 (dd, 1H, J=13, 7 Hz), 3.24 (dd, 1H, J=13, 8 Hz), 3.13-3.04 (m, 1H), 2.58 (s, 3H).

Workup

  1. washwashed in sucession with 30 mL of 2.0 N aqueous HCl, 30 mL of saturated aqueous sodium bicarbonate, and 30 mL of brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with 20-30% of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-74b1472cd0ed4c91958eccdfe92169fe
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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