Methyl iodide → HCID 68453284, compound

HRID 2357357Notes

Reaction equation

[Mg].CI.C[O:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]([O:17]C)[C:7]=1[C@H:19]1[C@H:24]([C:25]([CH3:27])=[CH2:26])[CH2:23][CH2:22][C:21](=[CH2:28])[CH:20]1[OH:29]>CCOCC>[OH:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]([OH:17])[C:7]=1[C@H:19]1[C@H:24]([C:25]([CH3:27])=[CH2:26])[CH2:23][CH2:22][C:21](=[CH2:28])[CH:20]1[OH:29]

Participants

Conditions

Temperature: 210 °C

Procedure

A Grignard reagent was prepared with magnesium (84 mg, 3.5 mmol) and CH3I (0.2 ml, 3.5 mmol) in dry ether (1 ml, distilled over sodium) under N2 atmosphere. (6a) (360 mg, 1 mmol) in ether (0.5 ml) was added to the stirred solution and the ether was distilled. The residue was heated under N2 atmosphere till 210° C. for 45 min. Then the flask was cooled till room temperature and the reaction was quenched with ice water. The aqueous solution was extracted several times with ether. The combined organic extracts were dried on MgSO4 and filtered. Removal of the solvents under reduced pressure afforded a residue that was chromatographed on silica gel (25% Ether/P.E.) to give 132 mg of the pure (11a) (yield 40%).

Workup

distillationthe ether was distilled
temperatureThen the flask was cooled till room temperature
customthe reaction was quenched with ice water
extractionThe aqueous solution was extracted several times with ether
customThe combined organic extracts were dried on MgSO4
filtrationfiltered
customRemoval of the solvents under reduced pressure
customafforded a residue that
customwas chromatographed on silica gel (25% Ether/P.E.)

Sources & evidence

ORD record: ord-ab3d850aef7c4fee949a9a73e2f5d2ac
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759526B2

Reaction notes

Loading…