Dichloromethane → HCID 19876740, compound

HRID 1886016Notes

Reaction equation

HRID 1886016 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][OH:12].[OH-].[Na+].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.ClCCl>O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:12][CH2:11][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 19876769HCID 19876769, compound

Product 1

HCID 19876740HCID 19876740, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-benzoxazoleethanol (1.46 g), 50% sodium hydroxide (3 ml), 1,6-dibromohexane (3 ml), TAB (100 mg) and dichloromethane (2 ml) was vigorously stirred at room temperature for 22 h, diluted with water (15 ml) and extracted with ether (40 ml). The organic phase was washed with brine (10 ml), dried and evaporated in vacuo. The residual oil was purified by FCC. Elution with hexane and hexane-ether (19:1) followed by hexane-ether (2:1) and ether gave the title compound as a pale yellow oil (1.60 g) which solidified on refrigeration.

Workup

  1. extractionextracted with ether (40 ml)
  2. washThe organic phase was washed with brine (10 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customThe residual oil was purified by FCC
  6. washElution with hexane and hexane-ether (19:1)

Sources & evidence

ORD record
ord-5dc753111c3c4e30a49ade8345c82913
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

Loading…