HCID 12160525, compound → HCID 59779169, compound

HRID 1096736Notes

Reaction equation

HRID 1096736 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][CH:13]=[O:14].[CH2:15]([Mg]Br)[CH:16]=[CH2:17]>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][CH:13]([OH:14])[CH2:17][CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 12160525HCID 12160525, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 59779169HCID 59779169, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(naphthalen-2-yl)propiolaldehyde (3.97 g, 22.0 mmol) in tetrahydrofuran (250 mL) was added to a solution of allyl magnesium bromide (33.1 mL, 33.0 mmol, 1.5 eq.) at 0° C. over 25 min. Stirring was continued overnight and the reaction was carefully quenched with water (50 mL) at 0° C. tert-butyl methyl ether (100 mL) was added, and the layers were stirred and allowed to separate. The aqueous phase was re-extracted with tert-butyl methyl ether (50 mL) and the combined organic layers were dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo. Purification by silica gel chromatography using 1:6 ethyl acetate/petrol as the eluting solvent to afford the desired compound (2.30 g, 47%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.58-2.65 (2H, m, CH2), 4.71 (1H, t, J=6.3 Hz, CH), 5.24-5.31 (2H, m, CH2), 5.95-6.06 (1H, m, CH), 7.46-7.51 (3H, m, ArH), 7.76-7.83 (3H, m, ArH), 7.96 (1H, s, ArH).

Workup

  1. customthe reaction was carefully quenched with water (50 mL) at 0° C. tert-butyl methyl ether (100 mL)
  2. additionwas added
  3. stirringthe layers were stirred
  4. customto separate
  5. extractionThe aqueous phase was re-extracted with tert-butyl methyl ether (50 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-26052cd0a8c440cb889f7f6ae9cda506
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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