Hydrochloric Acid → HCID 20147162, compound

HRID 569482Notes

Reaction equation

HRID 569482 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.CCCCCC.Br[C:21]1[O:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=1.Cl>C1COCC1.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.[Cl-].[Zn+2].[Cl-]>[C:1]([C:21]1[O:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 123701-OctyneHCID 6003285-Bromofuran-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 20147162HCID 20147162, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent4×HCID 178418397HCID 178418397, compoundSolvent

Procedure

To a solution of 1-octyne (5.5 g, 50 mmole) in dry THF (40 ml) at -30° C. was added n-butyl lithium in hexane (1.05 eq). After warming to 0° C. over 1 hr a solution of zinc chloride (6.95 g, 50 mmole) in THF (50 ml) was added and temperature raised to room temperature over 1/2 hr. Sequentially, solutions of 5-bromofuran-2-carboxaldehyde (8.75 g, 50 mmole) in THF (20 ml) and tetrakis triphenylphosphinepalladium (0) (5.7 g, 10%) in THF (50 ml) were added. The mixture was heated to reflux for 2 hr after which it was cooled and added to dilute hydrochloric acid (50 ml). After extracting into diethyl ether (3×100 ml), drying the ethereal solution (MgSO4) and removing the solvent under reduced pressure, the resulting oil was chromatographed on silica (DCM: Hexane 1:2) to give the title compound 6.83 g (67 %) as an oil. νmax (film) 3150, 3125, 2225, 1680, 890, 770; δ(CDCl3)0.90(3H, distorted t), 1.42(8H, complex m), 2.45(2H, t, J=6.5 Hz), 6.60(1H, d, J=3.0 Hz), 9.65(1H, s).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 hr after which it
  4. temperaturewas cooled
  5. extractionAfter extracting into diethyl ether (3×100 ml)
  6. dry with materialdrying the ethereal solution (MgSO4)
  7. customremoving the solvent under reduced pressure
  8. customthe resulting oil was chromatographed on silica (DCM: Hexane 1:2)

Sources & evidence

ORD record
ord-1d4987d17b4e4887a1aac09475d422ae
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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