Diboron → HCID 20131147, compound

HRID 1380131Notes

Reaction equation

HRID 1380131 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:13](O)=[O:14])=[CH:5][CH:4]=1.B#B>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:13][OH:14])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6328200DiboronHCID 13590274HCID 13590274, compound

Product 1

HCID 20131147HCID 20131147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-(4-methoxyphenyl)-2-[2-(4-methoxy phenyl)ethyl]pentanoic acid (20 g, 0.058 mol) in dry tetrahydrofuran (50 ml) was treated with a solution of diborane in tetrahydrofuran (100 ml of 1M, 0.1 mol) and left to stand at room temperature for 10 hours. The solvent was evaporated off under reduced pressure and the residue was acidified with hydrochloric acid (2N) and extracted with chloroform. The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was further purified by column chromatography (silica gel, ethyl acetate) to give 5-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)ethyl]-1-pentanol as a colourless oil.

Workup

  1. waitleft
  2. customThe solvent was evaporated off under reduced pressure
  3. extractionextracted with chloroform
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customthe solvent was evaporated off under reduced pressure
  6. customto give the crude product which
  7. customwas further purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-0904281a24644576936a05b598582284
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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