HCID 57435888, compound → 931430-20-5

HRID 30580Notes

Reaction equation

HRID 30580 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1.[H][H]>[Pt]=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57435888HCID 57435888, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57435887931430-20-5Yield 74%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A mixture of an ethanolic solution of 5-(3-Bromo-phenyl)-pent-4-yn-1-ol (Example 3, step a) (1 g, 4.2 mmol)and platinum oxide (24 mg, 10% mol) was placed on a parr shaker for 4 hrs under 40 psi of hydrogen. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo. The resultant residu was purified by flash chromatography on silica gel, 1st 10:1 hexane/ ethyl acetate, 2nd 2:1 hexane/ethyl acetate as eluent, to give 5-(3-bromophenyl)pentan-1-ol as a clear oil, 0.75 g (74% yield); 1H NMR (DMSO-d6) δ 1.2 (m, 2H); 1.3 (m, 2H); 1.5 (m, 2 H); 3.3 (q, 2H); 4.3 (t, 1 H); 7.2 (m, 2 H); 7.4 (m, 2 H) MS [(+)ESI] m/z=243 [M−H]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe resultant residu was purified by flash chromatography on silica gel, 1st 10:1 hexane/ ethyl acetate, 2nd 2:1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-bfb46ea0b2f246ce94355b728aa1628e
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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