Sodium hydride → HCID 59557729, compound

HRID 1175323Notes

Reaction equation

HRID 1175323 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22].[H-].[Na+].Br[CH2:26][C:27]#[C:28][CH3:29]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][O:22][CH2:26][C:27]#[C:28][CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 595577063-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol

Product 1

HCID 59557729HCID 59557729, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol (BL) (0.268 g, 0.70 mmol) in 5 mL of THF was added NaH (0.034 g, 0.84 mmol, 60%) and stirred for 40 min. 1-bromo-2-butyne (0.094 mL, 1.05 mmol) was added and the mixture was stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated and purified by preparative TLC (eluting with EtOAc:PE=1:10) to obtain 0.2 g of intermediate BM.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by preparative TLC (eluting with EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-754414dff5ca4009b086c461394b7518
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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