Triethylamine → HCID 88876334, compound

HRID 2091602Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[N:13]/[OH:14])/[CH2:7][C:8]32[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[CH3:22][S:23]([O:14]/[N:13]=[C:6]1\[CH2:7][C:8]2([CH2:12][CH2:11]2)[C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of (E)-6′-bromospiro[cyclopropane-1,1′-inden]-3′(2′H)-one oxime (500 mg, 1.98 mmol) in THF (5 mL) was added triethylamine (332 μL, 2.38 mmol) followed by slow addition of MsCl (170 μL, 2.18 mmol). The reaction was stirred 10 minutes at 0° C. then concentrated. The residue was triturated from methanol (5 mL) to afford (E)-6′-bromospiro[cyclopropane-1,1′-inden]-3′(2′H)-one O-methylsulfonyl oxime (653 mg, 100% yield) as a white solid after drying under high vacuum. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.64 (d, J=8.4 Hz, 1H), 7.42 (dd, J=8.3, 1.6 Hz, 1H), 6.98 (d, J=1.5 Hz, 1H), 3.26 (s, 3H), 3.15 (s, 2H), 1.06-1.42 (m, 4H); MS (EI) m/z=331.2 [M+1]+.

Workup

concentrationthen concentrated
customThe residue was triturated from methanol (5 mL)

Sources & evidence

ORD record: ord-095bbec24b924cbfba0a42e5bc5c5681
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440652B2

Reaction notes

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