Methanol → HCID 15287671, compound

HRID 1885928Notes

Reaction equation

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

Participants

Reactant 2

HCID 887Methanol

HCID 15237330HCID 15237330, compound

Product 1

HCID 15287671HCID 15287671, compound

Procedure

The compound of Example 5 (1.0 g, 0.0025 mole) was dissolved in methanol (35 ml) and hydrogen chloride gas was bubble into the solution for 10 minutes. Nitrogen gas was bubbled into the reaction solution to remove most of the dissolved hydrogen chloride, and then the reaction mixture was poured into water (150 ml). The mixture was extracted twice with 100 ml of diethyl ether, and the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography. The structure was supported by NMR, infrared spectroscopy and elemental analysis.

Workup

customhydrogen chloride gas was bubble into the solution for 10 minutes
customNitrogen gas was bubbled into the reaction solution
customto remove most of the dissolved hydrogen chloride
additionthe reaction mixture was poured into water (150 ml)
extractionThe mixture was extracted twice with 100 ml of diethyl ether
dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated to an oil with a rotary evaporator
customThe product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-ec988102302544a1976dec570abcda3c
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05147893

Reaction notes

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