Triethylamine → 4-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)benzonitrile

HRID 1016014Notes

Reaction equation

O[C:2]1([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.S(Cl)(C)(=O)=O>C(Cl)Cl>[O:6]1[C:5]2([CH2:10][CH2:11][C:2]([C:12]3[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=3)=[CH:3][CH2:4]2)[O:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 4-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)benzonitrile (7.8 g) in methylene chloride (100 mL) was added triethylamine (21 mL) at room temperature. The solution was cooled down to −40° C. and then mesyl chloride (4.7 mL) was added dropwise. The reaction mixture was stirred at 40° C. for 30 min, then warmed up to room temperature gradually and continuously stirred overnight. The reaction was quenched with sat. aqueous NaHCO3 solution. The aqueous layer was extracted with methylene chloride. The combined organic extracts were washed with brine, dried with Na2SO4, then evaporated. The residue was purified by column (Hex/EtOAc=5/1) to give the product 5.2 g as a white solid (yield: 71%): 1H NMR (CDCl3) δ 7.62-7.55 (2H, m), 7.50-7.45 (2H, m), 6.17-6.13 (1H, m), 4.02 (4H, s), 2.68-2.62 (2H, m), 2.53-2.47 (2H, m), 1.96-1.92 (2H, m); MS: 242 (M+1)+.

Workup

temperaturewarmed up to room temperature gradually
customcontinuously stirred overnight
customThe reaction was quenched with sat. aqueous NaHCO3 solution
extractionThe aqueous layer was extracted with methylene chloride
washThe combined organic extracts were washed with brine
dry with materialdried with Na2SO4
customevaporated
customThe residue was purified by column (Hex/EtOAc=5/1)

Sources & evidence

ORD record: ord-a80b8d45e6d742669c1a7669cbfb8182
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985730B2

Reaction notes

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