Tetrabutylammonium Fluoride → HCID 86761236, compound

HRID 2265236Notes

Reaction equation

HRID 2265236 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@H:8]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])[C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH3:10])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.Cl>[Cl:18][C:13]1[CH:12]=[C:11]([C@@H:9]([CH3:10])[C@@H:8]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:7][OH:6])[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86761235HCID 86761235, compound

Product 1

HCID 86761236HCID 86761236, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2R,3R)-1-(tert-butyl-dimethyl-silyloxy)-3-(3,4-dichloro-phenyl)-2-methanesulfonyloxy-butane (4.99 g, 11.7 mmol) in THF (117 mL) at 0° C. was added tetrabutylammonium fluoride (TBAF; 1.0 M in THF, 23.4 mL). The solution was stirred at 0° C. for 15 min, then was diluted with 1 N HCl (100 ml) and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield a yellow oil. The product was purified by flash chromatography (EtOAc/hexanes) to give 3.45 g (94%) of the desired product. 1H NMR (400 MHz, CDCl3): 7.41 (d, J=8.0, 1H), 7.35 (d, J=2.0, 1H), 7.12 (dd, J=8.2, 2.4, 1H), 4.82-4.78 (m, 1H), 3.88-3.84 (m, 1H), 3.74-3.69 (m, 1H), 3.17 (q, J=7.1, 1H), 2.78 (s, 3H), 1.98 (br s, 1H), 1.36 (d, J=7.2, 3H).

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customto yield a yellow oil
  5. customThe product was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-ad6276f3b6334e40ba908e601f5e52f9
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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