1,4-Butanediol → HCID 11390490, compound

HRID 2103745Notes

Reaction equation

HRID 2103745 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[Cl:7][C:8]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>>[Cl:7][C:8]1[CH:15]=[C:14]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 11390490HCID 11390490, compoundYield 4.4%

Procedure

Following the procedure described for Example 29, 1,4-butanediol (1 mL, 10 mmol) was reacted with 2-chloro-4-fluoro-benzonitrile (159 mg, 1.0 mmol) for 24 hours at room temperature. Purification by reverse phase high pressure chromatography eluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water) provided 10 mg of 2-chloro-4-(4-hydroxy-butoxy)-benzonitrile. 1H NMR (CDCl3) δ 7.54 (d, 1H), 6.98 (d, 1H), 6.83 (dd, 1H), 4.03 (t, 2H), 3.71 (t, 2H), 1.90 (m, 2H), 1.72 (m, 2H); MS 226.1 (M+1).

Workup

  1. customPurification by reverse phase high pressure chromatography
  2. washeluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water)

Sources & evidence

ORD record
ord-a4caa1e03d1e4ca4a5c4a678b7f4bea3
Source dataset
uspto-grants-2009_08
Patent number
US07576128B2

Reaction notes

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