Tetrabutylammonium Fluoride → HCID 58230572, compound

HRID 390396Notes

Reaction equation

HRID 390396 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](C)(C)[O:22][SiH2]C(C)(C)C)=[C:17]([O:30][CH3:31])[CH:16]=2)=[CH:9][C:8]=1[F:32])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:32][C:8]1[CH:9]=[C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[C:17]([O:30][CH3:31])[CH:16]=2)[CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131730264HCID 131730264, compound

Product 1

HCID 58230572HCID 58230572, compoundYield 131.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxy-benzyloxy]-2-fluoro-phenyl}-propionic acid ethyl ester (1 g, 2.1 mmol) in THF (15 mL) is added tetra-n-butylammoniumfluoride (1 M in THF, 3.15 mL, 3.15 mmol) at 0° C. and the reaction mixture is stirred for 2 hour at 25° C. The reaction mixture is quenched with water and concentrated. The residue is diluted with EtOAc, washed with water (15 mL) and brine (15 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (1.0 g, crude). The crude product is used without further purification.

Workup

  1. customThe reaction mixture is quenched with water
  2. concentrationconcentrated
  3. additionThe residue is diluted with EtOAc
  4. washwashed with water (15 mL) and brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-320ee7baf74e49c69df742f7e855ac34
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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