Diboron → HCID 15617525, compound

HRID 2352118Notes

Reaction equation

HRID 2352118 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].B#B>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 15617524HCID 15617524, compound

Product 1

HCID 15617525HCID 15617525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(7-bromoheptyl) benzoic acid (8.0 g, 0.027 mole) and distilled tetrahydrofuran (75 ml) was added diborane (40 ml, 0.04 mole) at room temperature under argon. The reaction mixture was stirred at room temperature for approximately 18 hours under argon, cooled to 0° C. and quenched with ethanol. The solvents were evaporated to give a colorless oil which was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulfate and filtered. The resulting oil was flash chromatographed on silica using 10% ethyl acetate in hexane to give the desired product.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ethanol
  3. customThe solvents were evaporated
  4. customto give a colorless oil which
  5. customwas partitioned between methylene chloride and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customchromatographed on silica using 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8fac73da05db4b9e8dcd3fcb3fc77518
Source dataset
uspto-grants-1989_10
Patent number
US04874792

Reaction notes

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