Tetrahydrofuran → HCID 86739520, compound

HRID 1462127Notes

Reaction equation

HRID 1462127 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].C(N(CC)CC)C.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.[O:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>>[CH:33]1([C:36]([O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][S:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([O:1][C:43]([CH:42]4[CH2:40][CH2:41]4)=[O:39])=[C:3]([N+:23]([O-:25])=[O:24])[CH:4]=3)(=[O:11])=[O:10])=[CH:14][C:15]=2[N+:20]([O-:22])=[O:21])=[O:37])[CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 86739519HCID 86739519, compound

Product 1

HCID 86739520HCID 86739520, compound

Procedure

32.6 g of 4-hydroxy-3-nitrophenylmethylsulfone are suspended in 250 ml of tetrahydrofurane and to this suspension are added 21 ml of triethylamine. With stirring, 15.7 g of cyclopropanecarboxylic acid chloride are added dropwise to the resultant solution. After the weakly exothermic reaction has subsided, stirring is continued for 3 hours at room temperature and the filtrate is concentrated, affording 42 g of a viscous oil which is digested with petroleum ether. Yield: 40.5 g of pale yellow crystalline product with a melting point of 114°-116° C.

Workup

  1. customAfter the weakly exothermic reaction
  2. stirringstirring
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-58671858195641b4af5ccba1d13d7b30
Source dataset
uspto-grants-1984_07
Patent number
US04459152

Reaction notes

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