Tetrahydrofuran → HCID 23079270, compound

HRID 2080735Notes

Reaction equation

HRID 2080735 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 11-4 was dissolved in methanol (61 ml) and THF (31 ml) and added with sodium borohydride (0.442 g) under ice-cooling and the whole was stirred at room temperature for 2 hours. The reaction solution was added with a saturated aqueous ammonium chloride solution and then subjected to 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. temperaturecooling
  2. extractionsubjected to extraction with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4359a12870554bf49d4e39c6f5c3160a
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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