Isobutyl chloroformate → 4-Hydroxybiphenyl

HRID 1288068Notes

Reaction equation

HRID 1288068 reaction equation
CCCCC[C@H](O)/C=C/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20](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>[C:15]1([C:14]2[CH:13]=[CH:9][C:10]([OH:24])=[CH:11][CH:12]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5280363Dinoprost

Product 1

HCID 71034-Hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.535 g. of PGF2α, 0.254 ml. of triethylamine, 0.238 ml. of isobutylchloroformate, and 0.385 g. of p-phenylphenol, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate followed by acetonitrile. The residue obtained by concentration of selected fractions, 0.270 g., is crystallized from ethyl acetate diluted with an equal volume of hexane as the title compound, white free-flowing crystals, m.p. 114.3°-116.8° C. having Rf 0.25 (TLC on silica gel in ethyl acetate).

Sources & evidence

ORD record
ord-4ea52b9bf95e425b889f32195fede72b
Source dataset
uspto-grants-1976_10
Patent number
US03987067

Reaction notes

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