Triethylamine → 4-Hydroxy-9-fluorenone

HRID 1288073Notes

Reaction equation

CCCCC[C@H](O)/C=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18]CC(O)=O)[C@@H:12]([OH:23])[CH2:11][C@H:10]1O.C([O:30]C(Cl)=O)C(C)C.C(N([CH2:39][CH3:40])CC)C>>[OH:30][C:40]1[C:39]2[C:14]3[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:23])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 5280363Dinoprost

Product 1

HCID 161394-Hydroxy-9-fluorenone

Procedure

Following the procedure of Example 1 but using 0.738 g. of PGF2α, 0.347 ml. of triethylamine, 0.326 ml. of isobutylchloroformate, and 0.612 g. of 4-hydroxy-9-fluorenone, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-water (99:1) followed by ethyl acetate-acetone-water (70:30:1). The residue obtained by concentration of selected fractions, 0.650 g., is crystallized from ethyl acetate-hexane (10:7) as the title compound, white free-flowing crystals, m.p. 83.8°-86.8° C. having Rf 0.27 (TLC on silica gel in ethyl acetate).

Sources & evidence

ORD record: ord-bf5bf734c1c44eb4a0aed79d1963bc1b
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03987067

Reaction notes

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