Ethylene Glycol → HCID 21849014, compound

HRID 617700Notes

Reaction equation

HRID 617700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:14])[C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[C:12]=1[Cl:13].[CH2:15](O)[CH2:16][OH:17].C(OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([Cl:14])[C:5]2[S:10][CH2:9][CH2:8][C:7]3([O:17][CH2:16][CH2:15][O:11]3)[C:6]=2[C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 15278484HCID 15278484, compound

Product 1

HCID 21849014HCID 21849014, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15 g (0.048 mol) of the title compound of Step C, 150 mL of ethylene glycol, 100 mL of trimethyl orthoformate (purchased from Aldrich Chemical Company), and 0.06 g of p-toluenesulfonic acid monohydrate were stirred together at 80° C. under nitrogen overnight. The mixture was diluted with 250 mL of diethyl ether and washed with a 1:1 mixture of 1N sodium hydroxide:saturated aqueous NaCl (2×300 mL), saturated aqueous NaCl (1×500 mL), dried (Na2SO4), filtered, and evaporated to dryness. The crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate:hexane (0.5:9.5) to yield 8.39 g of the title compound of Step D as a solid melting at 152-153° C. 1H NMR (CDCl3): δ2.3 (m,2H), 3.0 (m,2H), 4.16 (m,2H), 4.37 (m,2H), 7.6 (s,1H).

Workup

  1. washwashed with a 1:1 mixture of 1N sodium hydroxide
  2. dry with materialsaturated aqueous NaCl (2×300 mL), saturated aqueous NaCl (1×500 mL), dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate:hexane (0.5:9.5)

Sources & evidence

ORD record
ord-eeed03d636c2470285b7e8c5a14c0571
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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