Thionyl Chloride → HCID 15703835, compound

HRID 1534371Notes

Reaction equation

HRID 1534371 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[O:9][C:10]3[C:15]([C:16]([O:18][CH2:19][C:4]=2[CH:3]=1)=[O:17])=[C:14]([O:20][CH3:21])[C:13]([C@@H:22](O)[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:12][CH:11]=3.S(Cl)([Cl:30])=O>O1CCOCC1>[Cl:30][CH:22]([C:13]1[CH:12]=[CH:11][C:10]2[O:9][C:5]3[C:6]([OH:8])=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=3[CH2:19][O:18][C:16](=[O:17])[C:15]=2[C:14]=1[O:20][CH3:21])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one

Product 1

HCID 15703835HCID 15703835, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

200 mg (0.54 mmol) of penicillide (Ib) are heated under reflux for 5 h (exclusion of moisture) in 1 ml of dioxane and 0.38 ml (5.2 mmol) of thionyl chloride. After evaporating in vacuo, the residue is taken up in methylene chloride, and the solution is washed with aqueous bicarbonate, then with water, dried and evaporated. Chromatography on silica gel Si60 in ether/petroleum ether=2:1 yields 187 mg (93% of theory) of colorless solid.

Workup

  1. customAfter evaporating in vacuo
  2. washthe solution is washed with aqueous bicarbonate
  3. dry with materialwith water, dried
  4. customevaporated
  5. customChromatography on silica gel Si60 in ether/petroleum ether=2:1 yields 187 mg (93% of theory) of colorless solid

Sources & evidence

ORD record
ord-766cefe857214b32b21cf5a4b2d1e18c
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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