Water → HCID 53969861, compound

HRID 579932Notes

Reaction equation

HRID 579932 reaction equation
[OH:1][B:2]1[O:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][O:3]1.[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)#[N:14].N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:1][B:2]2[O:3][CH2:4][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:6][O:7]2)=[O:20])=[CH:17][CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 20135197HCID 20135197, compound

Product 1

HCID 53969861HCID 53969861, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17.2 g of 2-hydroxy-5-pentyl-1,3,2-dioxaborinane (prepared from trichloroborane and 2-hydroxymethylheptan-1-ol, followed by hydrolysis), 16.6 g of 4-cyanobenzoyl chloride and 15 ml of pyridine in 500 ml of toluene are heated at reflux temperature for 4 hours. Water is added to the mixture, the phases are separated, the organic phase is washed with water, dried over sodium sulphate and evaporated, and (5-pentyl-1,3,2-dioxaborinan-2-yl) 4-cyanobenzoate is obtained.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customthe phases are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-a13e2170f368471bbea53eb2835d2f45
Source dataset
uspto-grants-1988_06
Patent number
US04751017

Reaction notes

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