Ammonium Chloride → 1-(Benzyloxy)pent-4-en-2-ol

HRID 1600088Notes

Reaction equation

[C:1]1([CH2:7][O:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([Mg]Br)[CH:13]=[CH2:14].[Cl-].[NH4+]>C(OCC)C>[C:1]1([CH2:7][O:8][CH2:9][CH:10]([OH:11])[CH2:14][CH:13]=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring 0° C. solution of 59.0 g of product from Example 1 in 375 ml of diethyl ether is added, dropwise, 432.24 ml of 1M allylmagnesiumbromide in ether. The reaction is stirred at 0° C. for 1 hour, followed by overnight stirring at room temperature. The reaction is cooledto 0° C., hydrolyzed with saturated ammonium chloride, and the layers are separated. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo to give the product as an oil. The crude oil is purified by Kugelrohr distillation (bath temperature 100° C.) to give 61.5 g of the desired product as a colorless oil. 1H NMR(CDCl3):δ 7.34(m,5H); 5.82(m,1H); 5.08(m,2H); 4.56(s,2H); 3.88(m,1H); 3.44(ABq,2H); 2.27(t,2H); 1.7(bs, 1H).

Workup

waitfollowed by overnight
stirringstirring at room temperature
customthe layers are separated
washThe organic layer is washed with saturated sodium chloride
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b651b994bd44405da9f19dea8be29d34
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05744465

Reaction notes

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