Methyl iodide → HCID 69732452, compound

HRID 2180600Notes

Reaction equation

[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])C)[C:3]=1[O:20][CH2:21][CH3:22].C([N-][CH:27]([CH3:29])[CH3:28])(C)C.[Li+].CI>C1COCC1>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH:27]([CH3:28])[CH3:29])[C:3]=1[O:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-109, 512 mg, 1.4 mmol) in THF (10 mL) at −78° C. was added lithium diisopropylamide (1.5 M in cyclohexane, 2.0 mL, 3.0 mmol). The cold bath was removed and the mixture was stirred for 3 h. The mixture was cooled to −78° C. again and methyl iodide (0.52 mL, 8.34 mmol) was added. The mixture was stirred at room temperature for 16 h then quenched with ammonium chloride (sat), extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes) followed by HPLC (Waters-Nova Pak column, 2% ethyl acetate in hexanes) to give the title compound.

Workup

customThe cold bath was removed
stirringThe mixture was stirred at room temperature for 16 h
customthen quenched with ammonium chloride (sat)
extractionextracted with diethyl ether
washThe combined ethereal layers were washed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-ac0d837ba6d14f3d99b19f3f64226412
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

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