Sodium hydride → HCID 18423651, compound

HRID 2270118Notes

Reaction equation

HRID 2270118 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-b04de97298014c98b7ad402615780ece
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

Loading…