Ammonia → HCID 15078323, compound

HRID 1110839Notes

Reaction equation

HRID 1110839 reaction equation
[NH3:1].[CH:2]([S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH3:20])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5])=[CH2:3]>C(#N)C>[NH2:1][CH2:3][CH2:2][S:4]([C:7]1[CH:8]=[C:9]([C@H:21]2[CH2:25][CH2:24][C@H:23]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[O:22]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH3:20])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15078320HCID 15078320, compound

Product 1

HCID 15078323HCID 15078323, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Ammonia was bubbled into a solution of trans-2-(3-vinylsulfonyl-4,5-dipropoxyphenyl)-5-(3,4,5-trimethoxy-phenyl)tetrahydrofuran (30 mg, 0.06 mmol) at 0.5° C. for 3 min in acetonitrile (3 mL). The solution was then heated at 65° C. in a pressure bottle overnight, cooled, and evaporated to dryness. Purification by preparative TLC (CHCl3 -MeOH; 95:5, v/v) gave the title compound MS, m/z 538 (M+1)+. ; Rf 0.27; NMR (CDCl3) δ 1.05 & 1.09 (2 t J=7.5 Hz, 2 CH2CH2CH3), 3.58 (bt, SO2CH2CH2), 4.02 & 4.14 (2 t, J=6.5 Hz, 2 CH2CH2CH3), 5.16-5.28 (m, H-2 & H-5), 6.63 (s, 2 H, C5ArH), 7.27 & 7.48 (2 d, J=1.5 Hz, 2 H, C2ArH).

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. customPurification by preparative TLC (CHCl3 -MeOH

Sources & evidence

ORD record
ord-c3f428965f8c4a70b345ce325f66e22f
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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