Sodium hydride → HCID 18423651, compound

HRID 1282033Notes

Reaction equation

HRID 1282033 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH:5]([C:8]2[O:9][C:10]3[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4]1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>O1CCCC1>[C:21]([Si:18]([CH3:20])([CH3:19])[O:17][C:16]1[C:10]2[O:9][C:8]([CH:5]3[CH2:6][CH2:7][O:3][CH2:4]3)=[CH:12][C:11]=2[CH:13]=[CH:14][CH:15]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 18423661HCID 18423661, compound

Product 1

HCID 18423651HCID 18423651, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (80 mg, 60% dispersion in mineral oil) was added to a stirred solution of 2-(tetrahydrofuran-3-yl)-benzofuran-7-ol (0.37 g) in dry tetrahydrofuran (10 ml) at room temperature under a dry nitrogen atmosphere. After stirring for 10 minutes tert-butyldimethylsilyl chloride (0.27 g) was added and the reaction stirred for 90 minutes. The reaction mixture was partitioned between ethyl acetate (30 ml) and water (2×25 ml). The combined aqueous washings were extracted with ethyl acetate (30 ml). The organic extracts were combined, dried over magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow oil (0.58 g).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate (30 ml) and water (2×25 ml)
  3. extractionThe combined aqueous washings were extracted with ethyl acetate (30 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c128c46554ae4525b9293f37000c9ab2
Source dataset
uspto-grants-2002_09
Patent number
US06455561B1

Reaction notes

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