Toluene → (E)-3-Cyclopentyl-2-(4-(methylsulfonyl)phenyl)prop-2-EN-1-OL

HRID 2103608Notes

Reaction equation

CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[C:21](/[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1)=[CH:22]/[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)C>>[CH:23]1(/[CH:22]=[C:21](\[C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)/[CH2:20][OH:19])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Reactant 3

HCID 1140Toluene

HCID 14487Diisobutylaluminum hydride

HCID 67084405(E)-3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 53471256(E)-3-Cyclopentyl-2-(4-(methylsulfonyl)phenyl)prop-2-EN-1-OLYield 100.3%

Procedure

Following the method of example 54e, reaction of DIBAL in toluene (268 ml, 1.5 M, 402 mmol) with (E)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester (51.8 g, 160 mmol) affords the title compound as a solid (45 g). MS (m/e): 303.4 (M+Na).

Sources & evidence

ORD record: ord-b6105a0cdad74e06bd0108c7437e0024
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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