Methanesulfonyl chloride → HCID 59226499, compound

HRID 2192558Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH:11]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.C(OCC)(=O)C>[CH3:26][S:27]([O:16][CH:13]1[CH2:14][CH2:15][C:10]([C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:11][CH2:12]1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(3-nitropyridin-4-yl)cyclohex-3-enol (1.0 equiv.) and DIPEA (2.5 equiv.) in CH2Cl2 (0.15 M) was added methanesulfonyl chloride (1.8 equiv.) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. The reaction mixture was diluted with ethyl acetate (200 mL), and washed with sat NaCl (30 mL). The organic was dried MgSO4, filtered and concentrated to give 4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (93%). The residue was used in the next step without further purification. LC/MS (m/z): MH+=299.0, Rt=0.70

Workup

washwashed
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-cc2271caa0ba4f74bad3328951fa697c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329732B2

Reaction notes

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