Tetrahydrofuran → HCID 23136394, compound

HRID 1678608Notes

Reaction equation

HRID 1678608 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:31]=[C:32]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=1)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][C:18]=1[F:30])(C(C)(C)C)(C)C.C1COCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:30][C:18]1[CH:19]=[C:20]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:21]=[CH:22][C:17]=1[O:16][CH2:15][C:14]1[CH:31]=[C:32]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[C:12]([O:11][CH2:10][CH2:9][OH:8])[CH:13]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67373709HCID 67373709, compound

Product 1

HCID 23136394HCID 23136394, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Ethyl 3-(4-{[3-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-5-phenoxybenzyl]oxy}-3-fluorophenyl)propanoate (0.43 g, 0.75 mmol) was dissolved in a solution of tetrabutylammonium fluoride in THF (3 mL, 3.00 mmol), and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water, and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (0.25 g, yield 74%) as an oily matter.

Workup

  1. washwashed with water
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5)

Sources & evidence

ORD record
ord-c0b61054a628496e998e84315fa09c58
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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