3-(1-Naphthalenyl)-2-propynal → 1-Naphthalen-1-yl-hex-5-en-1-yn-3-ol

HRID 1096726Notes

Reaction equation

HRID 1096726 reaction equation
[C:1]1([C:11]#[C:12][CH:13]=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:15]([Mg]Br)[CH:16]=[CH2:17]>O1CCCC1>[C:1]1([C:11]#[C:12][CH:13]([OH:14])[CH2:17][CH:16]=[CH2:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 112408133-(1-Naphthalenyl)-2-propynalHCID 178455850HCID 178455850, compound

Product 1

HCID 597791081-Naphthalen-1-yl-hex-5-en-1-yn-3-olYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of naphthalen-1-yl-propynal (2.50 g, 13.88 mmol) in tetrahydrofuran (50 mL) was added to a stirred solution of allylmagnesium bromide (1M in diethyl ether, 20.81 mL, 20.81 mmol, 1.5 eq.) at 0° C. over 0.5 h under an atmosphere of nitrogen. Stirring was continued for a further 2 h at 0° C. The reaction was quenched with water (50 mL) at 0° C. To the reaction mixture was added diethyl ether (100 mL) and the reaction mixture was stirred and allowed to separate. The aqueous phase was re-extracted with diethyl ether (3×100 mL) and the combined organic layers were dried over sodium sulphate and concentrated in vacuo to afford a yellow oil. The crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%) to afford the desired compound as a yellow oil (2.34 g, 76%). 1H NMR (400 MHz, CDCl3) δ ppm 2.67-2.69 (2H, m, CH2), 4.80-4.81 (1H, m, CH), 5.24-5.31 (2H, m, CH2), 5.99-6.06 (1H, m, CH), 7.40-7.64 (4H, m, Ar—H), 7.66 (1H, d, J 8.0 Hz, ArH), 7.82 (1H, d, J 8.0 Hz, ArH), 8.28 (1H, d, J 8.0 Hz, ArH).

Workup

  1. customThe reaction was quenched with water (50 mL) at 0° C
  2. additionTo the reaction mixture was added diethyl ether (100 mL)
  3. stirringthe reaction mixture was stirred
  4. customto separate
  5. extractionThe aqueous phase was re-extracted with diethyl ether (3×100 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow oil
  9. customThe crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%)

Sources & evidence

ORD record
ord-538a82de4c154cf1a059363398a756d0
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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