1,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-ene → HCID 78135669, compound

HRID 626128Notes

Reaction equation

HRID 626128 reaction equation
[C:1]1([C:7]([CH2:23][CH3:24])=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31]O>>[CH3:25][N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:23][CH3:24])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 630591,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-eneHCID 978361-Methyl-2-pyrrolidinemethanol

Product 1

HCID 78135669HCID 78135669, compoundYield 33.2%

Procedure

Following same procedure of Mitsunobu reaction as described in example 16, step D, 4,4′-(2-phenylbut-1-ene-1,1-diyl)diphenol (220 mg, 0.473 mmol) was reacted with (1-methylpyrrolidin-2-yl)methanol (82 mg, 0.712 mmol, made from DL-proline Following Arch. Pharm. Phamz. Med. Chem. 1996, 329, 95-104.) to give 65 mg desired product (33% yield). m/z=414[M+1]+.

Workup

  1. customprocedure of Mitsunobu reaction

Sources & evidence

ORD record
ord-e2acb92f3431444ba70e40fd92164ba6
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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