Water → 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-[2-(phenylmethoxy)ethyl]furan

HRID 966898Notes

Reaction equation

HRID 966898 reaction equation
[CH3:1][C:2]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][CH2:8][C:9]1[O:10][C:11]([CH2:14][CH2:15][OH:16])=[CH:12][CH:13]=1)([CH3:4])[CH3:3].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:4][C:2]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][CH2:8][C:9]1[O:10][C:11]([CH2:14][CH2:15][O:16][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][CH:13]=1)([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 179623432-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-(2-hydroxyethyl)furan

Product 1

HCID 587458712-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-[2-(phenylmethoxy)ethyl]furanYield 82.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The alcohol 255C (1.00 g, 3.7 mmol) in 12 mL of THF was treated with 60% NaH (177.8 mg, 4.44 mmol), benzyl bromide (0.53 mL, 4.44 mmol) and tetrabutylammonium iodide (50 mg, 5%) for 3 h at rt. Water was added and the mixture was extracted with EtOAc (3×). The combined extracts were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 20% hexane/80% CH2Cl2 gave 1.10 g (3.05 mmol, 82.6%) of compound 255D as a yellow oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. washThe combined extracts were washed with water (1×) and brine (1×)
  3. dry with materialdried over Na2SO4
  4. customPurification by flash chromatography on silica gel eluting with 20% hexane/80% CH2Cl2

Sources & evidence

ORD record
ord-7401e3ba27ea43e4b8accbb5ccabcaf6
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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