3,4-dihydro-2H-pyran → HCID 86737123, compound

HRID 1277696Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH:7]([I:27])[CH:8]1[O:26][C@H:11]2[CH2:12][C@@H:13]([OH:25])[C@H:14](/[CH:15]=[CH:16]/[C:17]([OH:24])([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.[C:35](=[O:38])(O)[O-].[Na+]>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH:7]([I:27])[CH:8]1[O:26][C@H:11]2[CH2:12][C@@H:13]([O:25][CH:6]3[CH2:5][CH2:4][CH2:3][CH2:35][O:38]3)[C@H:14](/[CH:15]=[CH:16]/[C:17]([O:24][CH:34]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1

Participants

Conditions

Temperature: -4 °C

Procedure

To a solution of 1.067 g of (13E)-(5RS,6RS,9α,11α,15RS)-5-iodo-6,9-epoxy-11,15-dihydroxy-15-methylprost-13-enoic acid methyl ester [prepared as described in Reference Example 2(c)] in 20 ml of methylene chloride were added 1.4 mg of p-toluenesulphonic acid and 1.337 g of 2,3-dihydropyran and the mixture was stirred at -4° C. for 4.5 hours. The reaction mixture was then neutralised with an aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 1.2 g of the title compound having the following physical characteristics:

Workup

extractionextracted with chloroform
dry with materialThe extract was dried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel using
additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record: ord-1dca17e5d761426dba241e274f12ce53
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04278688

Reaction notes

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