Acetonitrile → HCID 12181446, compound

HRID 1088703Notes

Reaction equation

HRID 1088703 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15].C1(NC2CCCCC2)CCCCC1.C(#N)C>[Cu]I.CCOCC>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:15]#[C:14][CH2:13][CH2:12][OH:16]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7582DicyclohexylamineHCID 135663-Butyn-1-OLHCID 27627562-Bromoquinoline

Product 1

HCID 12181446HCID 12181446, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-bromoquinoline (0.44 g), 3-butynol (0.2 ml), N,N-dicyclohexylamine (0.46 ml), BTPC (30 mg), copper (I) iodide (5 mg) and acetonitrile (10 ml) was stirred at 22° for 5 h. Ether (50 ml) was added, and the mixture filtered and evaporated in vacuo. The residue was purified by FCC eluting with ether followed by ether-methanol (19:1), to afford the title compound as a colourless solid (0.41 g). A small sample recrystallised from ethyl acetate-hexane had m.p. 89°-91°.

Workup

  1. filtrationthe mixture filtered
  2. customevaporated in vacuo
  3. customThe residue was purified by FCC
  4. washeluting with ether

Sources & evidence

ORD record
ord-ecc6b053f04944ff85b724fce1cbe5fd
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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