Diiodomethane → 1-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

HRID 1745866Notes

Reaction equation

[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].I[CH2:22]I.[Cl-].[NH4+]>CCCCCC.C([Zn]CC)C>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of compound of formula (7), (12 g, 0.0447 mol) in dry hexane (50 ml), diethyl zinc (1.1 M solution in hexane, 185 ml) was added at 0° C. under nitrogen atmosphere followed by diiodomethane (18 ml, 0.224 mol). The reaction was stirred for 6 h at 0° C. and poured over cold aqueous solution of ammonium chloride. The organic layer was separated and the aqueous layer extracted repeatedly with diethyl ether. The combined organic layer was washed with aq. solution of sodium thiosulphate, dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified over silica gel column using ethyl acetate and light petroleum ether (1:50) as an eluent to afford compound of formula (8), as a colorless liquid 11.365 g (90%).

Workup

customThe organic layer was separated
extractionthe aqueous layer extracted repeatedly with diethyl ether
washThe combined organic layer was washed with aq. solution of sodium thiosulphate
dry with materialdried over anhydrous sodium sulphate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified over silica gel column

Sources & evidence

ORD record: ord-5954218747e140378d0ce94f946ceb2b
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019172B2

Reaction notes

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