Isobutyl chloroformate → 2-Naphthol

HRID 1077064Notes

Reaction equation

HRID 1077064 reaction equation
CCCCC[C@H](O)/C=C/[C@@H]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C@@H:12](O)[CH2:11][C@H]1O.C(OC(Cl)=O)C(C)C>C(N(CC)CC)C>[CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:20]=1[OH:22]

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5280363Dinoprost

Product 1

HCID 86632-Naphthol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.535 g. of PGF2 α , 0.254 ml. of triethylamine, 0.238 ml. of isobutylchloroformate, and 0.327 g. of β-naphthol, 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, 0.410 g., is crystallized from ethyl acetate diluted with 1.5 volumes of hexane as the title compound, white free-flowing crystals, m.p. 98.8°-100° C. having Rf 0.25 (TLC on silica gel in ethyl acetate).

Sources & evidence

ORD record
ord-599ff19c761d437d8b3248a433820986
Source dataset
uspto-grants-1976_05
Patent number
US03959319

Reaction notes

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