Dicyclohexylcarbodiimide → (2-Vinyl-4-iodophenyl)-4-methoxymethoxybenzoate

HRID 907588Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[CH2:5].[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:4]([C:3]1[CH:6]=[C:7]([I:10])[CH:8]=[CH:9][C:2]=1[O:1][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][O:12][CH3:11])=[CH:23][CH:22]=1)=[CH2:5]

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 2-hydroxy-5-iodostyrene, 4-(methoxymethoxy)benzoic acid, and DCC in methylene chloride at 23° C. was added DMAP, and the resulting mixture was stirred at 23° C. for 21 hours. The reaction mixture was then filtered over celite and concentrated in vacuo. Purification by flash chromatography (SiO2, hexanes:ethyl acetate 5:1) yielded (2-vinyl-4-iodophenyl)-4-methoxymethoxybenzoate as a colorless solid (4.6 g, 79%).

Workup

filtrationThe reaction mixture was then filtered over celite and
concentrationconcentrated in vacuo
customPurification by flash chromatography (SiO2, hexanes:ethyl acetate 5:1)

Sources & evidence

ORD record: ord-ca227d4138f649739768558ab134c84f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013203B2

Reaction notes

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