O-Xylene → 58551-69-2

HRID 1834054Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][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]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].[C:26]1(C)C(C)=CC=CC=1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@:6]([OH:25])(/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@@H:10]1[OH:24])[CH3:26]

Participants

Reactant 2

HCID 7237O-Xylene

HCID 5280363Dinoprost

Product 1

HCID 3502317758551-69-2

Procedure

Following the procedure of example 1 but substituting (15S) 15-methyl PGF2α for PGF2α and extending the reaction time in refluxing xylene from 24 hours to 48 hours there is produced crude (15S)-15-methyl PGF2α, 1,15-lactone. The crude lactone is purified by repeated chromatography and, further, if desired, by TLC purification to afford in low yield (15S)-15-methyl-PGF2α, 1,15-lactone in essentially pure form.

Sources & evidence

ORD record: ord-067f32b7c3f248c9a05693f10e48a45e
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04067991

Reaction notes

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