Water → HCID 23260609, compound

HRID 280912Notes

Reaction equation

HRID 280912 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 23260608HCID 23260608, compound

Product 1

HCID 23260609HCID 23260609, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.9 g of (S)-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 (S)-3-acetoxymethyl-1,2,3,4-tetrahydro-3-hydroxy-5,8-dimethoxy-1-oxo-naphthalene in the form of an off-white powder which was used in the next step without purification.

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-09c5b1dc404e47caab14c790793359bf
Source dataset
uspto-grants-1986_05
Patent number
US04591636

Reaction notes

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