Tetrahydrofuran → HCID 67776435, compound

HRID 705903Notes

Reaction equation

HRID 705903 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH2:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:17].B1C2CCCC1CCC2.C1C[O:30]CC1>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:30])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:17]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67776066HCID 67776066, compound

Product 1

HCID 67776435HCID 67776435, compoundYield 66.5%

Procedure

To the solution of 2-chloro-4-[(4-ethenylphenyl)oxy]-1-methylbenzene (2.8 g, 11.44 mmol) in dry THF (20 mL), was added 9-BBN (30 mL, 15.00 mmol) at 0° C. and stirred at room temperature overnight. Then the reaction mixture was quenched by addition of water (3 mL), followed by aq. NaOH (3M, 15 mL), and 30% H2O2 (15 mL). The reaction mixture was heated at 50° C. for 4 h. Then the THF and some water were removed under reduced pressure, and the residue was diluted with EA (30 mL). The organic layer was washed with water and brine, dried over Na2SO4 and concentrated. Purification via flash chromatography afforded the title compound (2 g, 66.5% yield). LCMS: rt=3.51 min, [M+H+]=245

Workup

  1. customThen the reaction mixture was quenched by addition of water (3 mL)
  2. temperatureThe reaction mixture was heated at 50° C. for 4 h
  3. customThen the THF and some water were removed under reduced pressure
  4. additionthe residue was diluted with EA (30 mL)
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-4ce40b22052e4ac99fbd98270d5d1c4f
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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