1,8-Octanediol → HCID 66745963, compound

HRID 471781Notes

Reaction equation

HRID 471781 reaction equation
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[N+:11]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([N+]([O-])=O)[C:15]=1[C:16]#[N:17])([O-:13])=[O:12].C1CCN2C(=NCCC2)CC1>C1COCC1>[OH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:10][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([N+:11]([O-:13])=[O:12])[C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 694201,8-OctanediolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 520718Dinitrobenzonitrile

Product 1

HCID 66745963HCID 66745963, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,8-octanediol (3.87 mmol, 566 mg) in THF (dry, 10 mL) was added 2,6-dinitrobenzonitrile (1.29 mmol, 250 mg) and DBU (1.30 mmol, 194 μL). The reaction mixture was stirred for 24 hours at room temperature an evaporated. The oily residue was triturated with 10% citric acid/water and solid NaCl added. The precipitate was collected, washed with water, dried in vacuo and purified on silica gel (40% to 100% EtOAc in hexanes) to give the desired product (235 mg, 62.3%) as a pinkish solid. MS 293 (MH+).

Workup

  1. customThe oily residue was triturated with 10% citric acid/water and solid NaCl
  2. additionadded
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried in vacuo
  6. custompurified on silica gel (40% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-02f1c6dfde0d4e62818c47b2b3b6c28c
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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