Chloroform → Acetate

HRID 372184Notes

Reaction equation

HRID 372184 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[C:19]2[C:14](=CC=C[CH:18]=2)[C:13]([CH2:20][O:21]C(C)=O)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2)=[O:3].[C:25]([O:29][C:30](=[O:33])[CH2:31][CH3:32])(=[O:28])[CH2:26][CH3:27].C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:2]([O-:4])(=[O:3])[CH3:1].[C:25]([O-:29])(=[O:28])[CH2:26][CH3:27].[C:20]([O-:21])(=[O:28])[C:13]1[CH:12]=[CH:7][CH:6]=[CH:19][CH:14]=1.[C:7]1([C:6]2[CH:5]=[CH:32][C:31]([C:30]([O-:29])=[O:33])=[CH:18][CH:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 3

HCID 6212ChloroformHCID 31263Propionic anhydrideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 4

HCID 175AcetateHCID 242BenzoateHCID 104745Propionate ionHCID 6931746HCID 6931746, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Starting from a 5α-alkoxymethyl-2β,4α-dihydroxy-cyclopentyl-1β-acetic acid-γ-lactone, wherein the alkoxy group is a methoxy, benzyloxy and p-methoxybenzyloxy group, esterification in pyridine with 1.3 molar equivalents of both acetic, acetic-formic or propionic anhydride and benzoyl or p-phenylbenzoyl chloride, gave the 4α-formate, acetate, m.p. 76°-77°, [α]D = - 29.5°, [α]365° = - 74°(CHCl3), propionate, benzoate and p-phenylbenzoate.

Sources & evidence

ORD record
ord-d0e469a048c04682a021e49b468f5d8e
Source dataset
uspto-grants-1978_05
Patent number
US04089896

Reaction notes

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