Isobutyl chloroformate → 4'-Hydroxyacetophenone

HRID 1288069Notes

Reaction equation

HRID 1288069 reaction equation
CCCCC[C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/C=C\CCCC(O)=O)[C@@H](O)[CH2:11][C@H:10]1[OH:24].C(OC(Cl)=O)C(C)C>C(N(CC)CC)C>[OH:25][C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:24])[CH3:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5280363Dinoprost

Product 1

HCID 74694'-Hydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.738 g. of PGF2α, 0.306 ml. of triethylamine, 0.288 ml. of isobutylchloroformate, and 0.299 g. of p-hydroxyacetophenone, 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-acetonitrile (1:1). The residue obtained by concentration of selected fractions, 0.589 g. is crystallized from ethyl acetate diluted with an equal volume of hexane as the title compound, white free-flowing crystals, m.p. 85.3°-86.5° C. having Rf 0.4 (TLC on silica gel in ethyl acetate-acetonitrile (4:1)).

Sources & evidence

ORD record
ord-e230bcb97c3e41ed85a199e038f957e0
Source dataset
uspto-grants-1976_10
Patent number
US03987067

Reaction notes

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