Diboron → HCID 68460742, compound

HRID 2197830Notes

Reaction equation

HRID 2197830 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](N)=[O:14])=[CH:11][CH:10]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.B#B.CCOCC.O>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:16][CH:17]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

5

Reactant 3

HCID 6328200DiboronHCID 21584184Diethylether waterHCID 67249721HCID 67249721, compound

Product 1

HCID 68460742HCID 68460742, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 84b (0.5 g, 1.73 mmol) was dissolved in THF (15 mL) and cooled in an ice bath. To the cold solution under nitrogen was added diborane as a 1.0M solution in THF (3.6 mL, 3.6 mmol) and the resulting mixture allowed to warm to room temperature and stir overnight. The crude product was isolated by extractive workup (ether/water) and dried with MgSO4, filtered and concentrated under vacuum giving the crude title compound. Purification by flash chromatography on silica gel gave the alcohol as a bright yellow solid (0.392 g, 82%).

Workup

  1. temperaturecooled in an ice bath
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customgiving the crude title compound
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-56ad68b8e88b4ee09d5342de61ae5db5
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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