Water → HCID 13264157, compound

HRID 1155495Notes

Reaction equation

HRID 1155495 reaction equation
[C:1]([O:4][CH2:5][C:6]1([OH:24])[CH2:15][C:14]2[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[C:8]2(SCCS2)[CH2:7]1)(=[O:3])[CH3:2].O.C([O:28]CC)C>O1CCCC1.CO>[C:1]([O:4][CH2:5][C:6]1([OH:24])[CH2:15][C:14]2[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[C:8](=[O:28])[CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 23320340HCID 23320340, compound

Product 1

HCID 13264157HCID 13264157, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.9 g of rac-3'-acetoxymethyl-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in 40 ml of tetrahydrofuran were added to a stirred suspension of 6.4 g of mercuric chloride and 6.4 g of mercuric oxide in 200 ml of methanol containing 18 ml of water. After standing at room temperature for 1 hour, ca 150 ml of solvent were removed by evaporation under reduced pressure, 200 ml of dichloromethane were added and the resulting suspension was filtered to remove insoluble material. 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 1.0 g (70%) of rac-3-acetoxymethyl-1,2,3,4-tetrahydro-3-hydroxy-5,8-dimethoxy-1-oxo-naphthalene in the form of an off-white powder of melting point 124°-126° C.

Workup

  1. customca 150 ml of solvent were removed by evaporation under reduced pressure, 200 ml of dichloromethane
  2. additionwere added
  3. filtrationthe resulting suspension was filtered
  4. customto remove insoluble material
  5. washThe filtrate was washed with three 200 ml portions of water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto give a solid residue

Sources & evidence

ORD record
ord-3506f652ff544f4e919a43cb04c9f329
Source dataset
uspto-grants-1981_11
Patent number
US04302398

Reaction notes

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