Methyl iodide → HCID 54523016, compound

HRID 1382369Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[C:6](=[O:7])[O:5][CH:4]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH3:26])[CH2:13][C:14]([OH:25])([CH3:24])[CH:15]([OH:23])[C:16]([CH3:22])=[CH:17][C:18]([O:20][CH3:21])=[O:19].[CH3:27]I>CCOC(C)=O.[Ag]=O>[CH3:27][O:1][CH2:2][CH:3]1[C:6](=[O:7])[O:5][CH:4]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH3:26])[CH2:13][C:14]([OH:25])([CH3:24])[CH:15]([OH:23])[C:16]([CH3:22])=[CH:17][C:18]([O:20][CH3:21])=[O:19]

Participants

Conditions

Temperature: 53 °C

Procedure

10 mg of methyl 11-(3-hydroxymethyl-4-oxo-2-oxetanyl)-4,5-dihydroxy-3,5,7-trimethyl-2-undecenoate in 2 ml of EtOAc was added 35 mg of silver oxide and 0.3 ml of methyl iodide. The mixture was heated at 53° C. overnight. The solution was filtered and concentrated by dryness. The product was purified by prep. TLC (EtOAc:Hexane=1:1) to afford methyl 11-(3-methoxymethyl-4-oxo-2-oxetanyl)-4,5-dihydroxy-3,5,7-trimethyl-2-undecenoate. ##STR26##

Workup

filtrationThe solution was filtered
concentrationconcentrated by dryness
customThe product was purified by prep

Sources & evidence

ORD record: ord-131b8f9314f74cf58613da190d7a20d2
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04806564

Reaction notes

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