Calcium Chloride → Trans-2-(4-allyloxy-5-amino-3-methoxyphenyl)-4-(3,4,5-trimeth-oxyphenyl)-1,3-dithiolane

HRID 260977Notes

Reaction equation

HRID 260977 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([C@H:14]2[S:18][C@H:17]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:16][S:15]2)=[CH:7][C:6]=1[O:31][CH3:32])[CH:2]=[CH2:3].[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Zn]>[CH2:1]([O:4][C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C@H:14]2[S:18][C@H:17]([C:19]3[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=3)[CH2:16][S:15]2)=[CH:7][C:6]=1[O:31][CH3:32])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 86749584Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Product 1

HCID 86749585Trans-2-(4-allyloxy-5-amino-3-methoxyphenyl)-4-(3,4,5-trimeth-oxyphenyl)-1,3-dithiolane

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane (24) 2.60 g, 5.43 mmole) was predissolved in 33 ml absolute ethanol. To this solution was added calcium chloride (0.602 g, 5.43 mmole) predissolved in 7 ml H2O followed by freshly activated zinc dust (7.09 g, 108 mmole). The reaction was refluxed for 12 hours. The solid was removed by vacuum filtration through celite and was washed with ethyl acetate. The filtrate was washed with 10% NaHCO3, dried over MgSO4, and

Workup

  1. temperatureThe reaction was refluxed for 12 hours
  2. customThe solid was removed by vacuum filtration through celite
  3. washwas washed with ethyl acetate
  4. washThe filtrate was washed with 10% NaHCO3
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-748b7a01d7264ac9a314cd52615b7bd7
Source dataset
uspto-grants-1996_06
Patent number
US05530141

Reaction notes

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