HCID 10765318, compound → HCID 10645065, compound

HRID 2399338Notes

Reaction equation

HRID 2399338 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([OH:28])[C@@:17]([OH:27])([C:23]([O:25]C)=[O:24])[CH2:18][C:19]([O:21]C)=[O:20]>Cl.O>[C:23]([C@:17]([OH:27])([C@@H:16]([OH:28])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:18][C:19]([OH:21])=[O:20])([OH:25])=[O:24]

Participants

4

Reactant 1

HCID 10765318HCID 10765318, compound

Product 1

HCID 10645065HCID 10645065, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

±(3R*,4S*) Methyl 11-(2,4-dichlorophenyl)-3,4-dihydroxy-3-methoxycarbonylundecanoate (189 mg, 0.434 mmol: prepared in analogous fashion to the higher homologue described in example 5) was heated under reflux in aqueous HCl (7.7M) for 3 h. The solution was cooled, diluted with water, and extracted with ether. The extracts were washed with aqueous NaOH, then the aqueous phase washed with ether, and acidified (aqueous HCl). The mixture was extracted with ether again. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum, and the residue recrystallised (ether/petroleum ether 40°-60° C.) to give the title compound (115 mg, 68%) as a white solid, m.p. 104°-105° C.

Workup

  1. temperaturewas heated
  2. temperatureThe solution was cooled
  3. extractionextracted with ether
  4. washThe extracts were washed with aqueous NaOH
  5. washthe aqueous phase washed with ether
  6. extractionThe mixture was extracted with ether again
  7. washThe extracts were washed with water, saturated aqueous NaCl
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed under vacuum
  10. customthe residue recrystallised (ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-25a2d77e81d3436fa76d0e339af00792
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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