Isobutyl chloroformate → 4-Hydroxybenzophenone

HRID 1288070Notes

Reaction equation

HRID 1288070 reaction equation
CCC[CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\CCCC(O)=O)[C@@H:12](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:5]=[CH:4][C:9]([C:10](=[O:24])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5280363Dinoprost

Product 1

HCID 143474-Hydroxybenzophenone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.738 g. of PGF2α, 0.291 ml. of triethylamine, 0.275 ml. of isobutylchloroformate and 0.594 g. of p-hydroxybenzophenone, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-water (99:1). The residue obtained by concentration of selected fractions, 0.492 g., is crystallized from ethyl acetate diluted with three volumes of hexane as the title compound, white free-flowing crystals, m.p. 73.8°-75.8° C., having Rf 0.5 (TLC on silica gel in ethyl acetate).

Sources & evidence

ORD record
ord-24c75405233942fc9b89f1ad6ee83326
Source dataset
uspto-grants-1976_10
Patent number
US03987067

Reaction notes

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