Tetrahydrofuran → HCID 57705499, compound

HRID 1662412Notes

Reaction equation

HRID 1662412 reaction equation
[CH3:1][C:2]([Si:5]([CH3:30])([CH3:29])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:9]=1)([CH3:4])[CH3:3].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[CH3:4][C:2]([Si:5]([CH3:29])([CH3:30])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23]([OH:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:9]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706379HCID 57706379, compound

Product 1

HCID 57705499HCID 57705499, compoundYield 80%

Procedure

To a stirred solution of 66.30A (0.500 g, 1.2 mmol) in THF (15.00 mL, 183 mmol) at 0° C. was added LAH in THF (2.3 mL, 2.3 mmol, 1.0M). The reaction was stirred for two hours. 1N NaOH(aq) was added to quench the reaction mixture, and the reaction was then extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.30B as a colorless oil (0.400 g, 80% yield).

Workup

  1. customto quench the reaction mixture
  2. extractionthe reaction was then extracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3ca36ddca474aefbf9febfd27df7790
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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