Ethanol → HCID 66730465, compound

HRID 1959965Notes

Reaction equation

HRID 1959965 reaction equation
C(O)C.[CH3:4][C:5]1([CH3:23])[C:9]([CH3:11])([CH3:10])[O:8][B:7]([C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([CH3:20])=[O:19])=[CH:14][CH:13]=2)[O:6]1.[BH4-].[Na+]>O>[CH3:11][C:9]1([CH3:10])[C:5]([CH3:4])([CH3:23])[O:6][B:7]([C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH:18]([OH:19])[CH3:20])=[CH:14][CH:13]=2)[O:8]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 66730457HCID 66730457, compound

Product 1

HCID 66730465HCID 66730465, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into ethanol (5.3 mL), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetone (530 mg, 1.92 mmol) synthesized in Reference Example 4 (4a) was dissolved, to which sodium borohydride (94 mg, 2.50 mmol) was added at 0° C., followed by stirring at room temperature for 30 minutes. To this reaction liquid, water was added, followed by extraction with dichloromethane. The resulting organic layer was dried over sodium sulfate and filtered, and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V) to give the desired title compound (483 mg, yield 91%).

Workup

  1. additionwas added at 0° C.
  2. additionwas added
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe resulting organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V)

Sources & evidence

ORD record
ord-3ceb50a6889e4b27853819ce9bbe48c5
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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