Diethyl Ether → HCID 13264154, compound

HRID 1155492Notes

Reaction equation

HRID 1155492 reaction equation
[CH2:1]1[CH2:6][O:5][C:3]([C:7]2([OH:25])[CH2:16][C:15]3[C:10](=[C:11]([O:19][CH3:20])[CH:12]=[CH:13][C:14]=3[O:17][CH3:18])[C:9]3(SCCS3)[CH2:8]2)([CH3:4])[O:2]1.C([O:28]CC)C>O1CCCC1.CO.O>[CH2:6]1[CH2:1][O:2][C:3]([C:7]2([OH:25])[CH2:16][C:15]3[C:10](=[C:11]([O:19][CH3:20])[CH:12]=[CH:13][C:14]=3[O:17][CH3:18])[C:9](=[O:28])[CH2:8]2)([CH3:4])[O:5]1

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 13264148HCID 13264148, compound

Product 1

HCID 13264154HCID 13264154, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of rac-3'-(1,1-ethylenedioxyethyl)-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in 20 ml of tetrahydrofuran were added over a period of 10 minutes to a suspension of 6.4 g of mercuric oxide and 6.4 g of mercuric chloride in 200 ml of methanol and 18 ml of water. The resulting suspension was stirred at room temperature for 1.25 hours and then ca 100 ml of solvent were removed by evaporation under reduced pressure. 300 ml of dichloromethane were added and the suspension obtained was filtered to remove insoluble mercury salts. The filtrate was washed with three 200 ml portions of water, dried over magnesium sulphate and evaporated to give a solid residue. Trituration with diethyl ether gave 1.42 g (89%) of rac-3-(1,1-ethylenedioxyethyl)-1,2,3,4-tetrahydro-3-hydroxy-5,8-dimethoxy-1-oxo-naphthalene in the form of an off-white powder of melting point 177.5°-178° C.

Workup

  1. customca 100 ml of solvent were removed by evaporation under reduced pressure
  2. addition300 ml of dichloromethane were added
  3. customthe suspension obtained
  4. filtrationwas filtered
  5. customto remove insoluble mercury salts
  6. washThe filtrate was washed with three 200 ml portions of water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give a solid residue

Sources & evidence

ORD record
ord-b2800489235a41a29d33d87681240db1
Source dataset
uspto-grants-1981_11
Patent number
US04302398

Reaction notes

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