Toluene → HCID 67084663, compound

HRID 2103599Notes

Reaction equation

HRID 2103599 reaction equation
C([O:3][C:4](=O)/[C:5](/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>>[CH2:25]([O:24][CH2:23][CH2:22][CH2:21][S:18]([C:15]1[CH:14]=[CH:13][C:12](/[C:5](=[CH:6]\[CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)/[CH2:4][OH:3])=[CH:17][CH:16]=1)(=[O:20])=[O:19])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 67084503HCID 67084503, compound

Product 1

HCID 67084663HCID 67084663, compoundYield 77.9%

Procedure

Following the method of example 54e, reaction of (E)-2-[4-(3-benzyloxy-propane-1-sulfonyl)-phenyl]-3-cyclopentyl-acrylic acid ethyl ester (2.05 g, 4.49 mmol) with DIBAL in toluene (9.43 mL, 11.2 mmol) and 1 h at ambient temperature gives the title compound as an oil (1.45 g). MS (m/e): 415 (M+H).

Sources & evidence

ORD record
ord-92362f9187e8456c8adaba07eb6e54fe
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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