Allyl bromide → 2-(Pent-4-en-1-ynyl)decahydronaphth-2-ol

HRID 634981Notes

Reaction equation

[C:1]([C:3]1([OH:13])[CH2:12][CH2:11][CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4]1)#[CH:2].[OH-].[K+].[CH2:16](Br)[CH:17]=[CH2:18]>CC(O)C.CO.Cl[Cu].C([O-])([O-])=O.[K+].[K+]>[C:1]([C:3]1([OH:13])[CH2:12][CH2:11][CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4]1)#[C:2][CH2:18][CH:17]=[CH2:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-ethynyldecahydronaphthalen-2-ol (100.6 g, 0.56 mol) in iPrOH (300 ml) was added slowly at 0° C. under a nitrogen atmosphere to a mixture of KOH (47.5 g), K2CO3 (6.5 g), and CuCl (4.4 g) in MeOH (300 ml). After stirring for additional 30 minutes at 0° C., allylbromide (102 g, 0.85 mol) was added slowly over a period of 25 minutes. The reaction mixture was stirred overnight at RT, quenched with NH4Cl and concentrated in vacuo. The residue was taken up in saturated NH4Cl (500 ml) solution, extracted with MTBE (2×400 ml). The combined organic phases were washed with saturated NH4Cl solution (500 ml), H2O (2×500 ml), saturated NaCl solution (500 ml) until neutral pH was achieved, dried (MgSO4), and evaporated in vacuo to yield quantitatively 120 g of crude product which was used without further purification in the next step.

Workup

stirringThe reaction mixture was stirred overnight at RT
customquenched with NH4Cl
concentrationconcentrated in vacuo
extractionextracted with MTBE (2×400 ml)
washThe combined organic phases were washed with saturated NH4Cl solution (500 ml), H2O (2×500 ml), saturated NaCl solution (500 ml) until neutral pH
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-2b759e789f024ddf88c897c10e51490b
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184419B2

Reaction notes

Loading…