HCID 19786181, compound → HCID 22848195, compound

HRID 1656874Notes

Reaction equation

HRID 1656874 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:23])[CH2:16][CH2:17][C:18]([O:20]CC)=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[O:23][C:18](=[O:20])[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 1

HCID 19786181HCID 19786181, compound

Product 1

HCID 22848195HCID 22848195, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-(4-heptyloxyphenyl)-4-hydroxybutanoate (17 g), porcine pancreatic lipase (hereinafter abbreviated to PPL) (34.4 g) and anhydrous diethyl ether (500 ml) were placed in a 1 l three-necked flask(followed by agitating the mixture at room temperature for 4 days, filtering off PPL, concentrating the filtrate under reduced pressure, and purifying the concentrate according to chromatography, to obtain rel-(S)-γ-(4-heptyloxyphenyl)-γ-butyrolactone (4 g) (69% e.e., optical purity (%) was measured by Chiral Cell OB made by Daisel Co., Ltd., e.e.: abbreviation of enantiomer excess, hereinunder this applies to) and ethyl rel-(R)-γ-(4-heptyloxyphenyl)hydroxybutanoate (5.2 g) ([α]D26.0 -13.69 (c 10.24, chloroform)). The former was recrystallized from ethanol, followed by removing the resulting crystals, concentrating the mother liquor under reduced pressure and recrystallizing the concentrate from ethanol to obtain rel-(S)-γ-(4-heptyloxyphenyl)-γ-butyrolactone (3.8 g) (95% e.e.). m.p.: 44.0° C., [α]D31.6 +6.62 (c 11.89, chloroform).

Workup

  1. filtrationfiltering off PPL
  2. concentrationconcentrating the filtrate under reduced pressure
  3. custompurifying the concentrate

Sources & evidence

ORD record
ord-0eb20be043ae40789bb3c2d325ab1839
Source dataset
uspto-grants-1993_10
Patent number
US05256330

Reaction notes

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