Tetrahydrofuran → HCID 23079270, compound

HRID 1174018Notes

Reaction equation

HRID 1174018 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5]2.C1COCC1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:5]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23079212HCID 23079212, compound

Product 1

HCID 23079270HCID 23079270, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (2.03 g) obtained in Example 127-4 was dissolved in methanol (60.9 ml) and THF (30.5 ml) and, under ice-cooling, added with sodium borohydride (0.442 g), followed by stirring at room temperature for 2 hours. The reaction solution was added with a saturated aqueous ammonium chloride solution and then subjected to separation/extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.54 g) as a yellow oily substance.

Workup

  1. extractionsubjected to separation/extraction with chloroform
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c301779befd4cd9a46897e9fd3d8827
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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