Triethylamine → HCID 18944187, compound

HRID 1181431Notes

Reaction equation

HRID 1181431 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10]([OH:14])[CH2:11][C:12]#[CH:13].C(N(CC)CC)C>CN(C)C=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:14][CH2:10][CH2:11][C:12]#[C:13][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 811292-Bromobenzaldehyde

Product 1

HCID 18944187HCID 18944187, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromobenzaldehyde (10 g, 54 mmol) in anhydrous N,N-dimethylformamide (150 ml) was added 3-butyn-1-ol (6.13 ml, 81 mmol) and triethylamine (11.3 ml, 81 mmol), followed by copper (I) iodide (490 mg, 5.4 mmol) and Pd(PPh3)2Cl2 (1.9 g, 2.7 mmol), and the mixture degassed three times and stirred at room temperature overnight. The mixture was poured into water (600 ml) and extracted with EtOAc (3×150 ml); the combined EtOAc layers were washed with water (2×250 ml), sat NaCl (100 ml), then dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica eluting with 50% Et2O in isohexanes to give the title compound (8.5 g, 90%) as an orange oil.

Workup

  1. customthe mixture degassed three times
  2. additionThe mixture was poured into water (600 ml)
  3. extractionextracted with EtOAc (3×150 ml)
  4. washthe combined EtOAc layers were washed with water (2×250 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica eluting with 50% Et2O in isohexanes

Sources & evidence

ORD record
ord-a5ec7b1d18ad44eaa15cba503a598fa3
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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