Tetrabutylammonium Fluoride → 2-(2-Hydroxyethyl)-5-[2-(phenylmethoxy)ethyl]furan

HRID 966899Notes

Reaction equation

HRID 966899 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C)(C)[O:24][CH2:25][CH2:26][C:27]1[O:28][C:29]([CH2:32][CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:31]=1)(C)C>C1COCC1>[OH:24][CH2:25][CH2:26][C:27]1[O:28][C:29]([CH2:32][CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 587458712-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-[2-(phenylmethoxy)ethyl]furan

Product 1

HCID 218751402-(2-Hydroxyethyl)-5-[2-(phenylmethoxy)ethyl]furanYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0M in THF, 3.06 mL, 3.06 mmol) was added to the solution of compound 255D (1.1 g, 3.06 mmol) in 10 mL of THF at 0° C. The reaction mixture was stirred at rt for 10 minutes, quenched by sat. NH4Cl and extracted with ether (3×). The combined extracts were dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 10% EtOAc/90% CH2Cl2 gave 750 mg (3.05 mmol, 99.6%) of compound 255E as a light yellow oil.

Workup

  1. customquenched by sat. NH4Cl
  2. extractionextracted with ether (3×)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. customPurification by flash chromatography on silica gel eluting with 10% EtOAc/90% CH2Cl2

Sources & evidence

ORD record
ord-b49a0c6294a543e6aab4d7d3ee30ef10
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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