Ethynyltributyltin → 2-(4-Ethynyl-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazole

HRID 2035680Notes

Reaction equation

HRID 2035680 reaction equation
[C:1]([Sn](CCCC)(CCCC)CCCC)#[CH:2].Br[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][C:25]([CH3:28])=[N:26][N:27]=2)=[C:19]([O:29][CH3:30])[CH:18]=1>C1COCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][C:25]([CH3:28])=[N:26][N:27]=2)=[C:19]([O:29][CH3:30])[CH:18]=1)#[CH:2]

Participants

6

Reactant 2

HCID 621176EthynyltributyltinHCID 597999112-(4-Bromo-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 580636252-(4-Ethynyl-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazoleYield 50%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

Pd(Ph3P)4 (100 mg, 0.087 mmol) and ethynyltributylstannane (600 mg, 1.904 mmol) was treated with a solution of 2-(4-bromo-2-methoxyphenyl)-5-methyl-1,3,4-oxadiazole (457.7 mg, 1.701 mmol) in 10 ml of THF and heated to 120° C. for 15 minutes in a microwave. The reaction was dissolved in brine and extracted three times with EtOAc. Organics were combined, dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel (100% hexanes followed by 0-25% EtOAc/DCM) gave a cream-colored solid (180 mg, 0.850 mmol, 49%).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3668f3f181bf4d48a026df46a223c0d4
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

Loading…