Diisobutylaluminum hydride → 3-(4-{2-[4-(Methylsulfonyl)phenyl]ethoxy}phenyl)-2-(phenylthio)propan-1-ol

HRID 987134Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22](OCC)=[O:23])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C[AlH]CC(C)C)C>ClCCl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([S:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:22][OH:23])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: -78 °C

Procedure

Ethyl 3-(4-{2-[4-(methylsulfonyl)phenyl]ethoxy} phenyl)-2-(phenylthio)propanoate (0.58 g, 1.20 mmole) was dissolved in dry dichloromethane (15 ml). The solution was cooled to −78° C. and DIBAL-H (1M hexan solution, 3.0 ml, 3.0 mmole) was added. The cooling agent was removed after 20 min. After 2 h the reaction mixture was cooled on an ice-bath before the addition of HCl (1M, 15 ml). The mixture was extracted with dicloromethane, the organic phase was washed twice with water (15 ml) and dried with NaSO4. Evaporation gave 0.554 g, ˜100%; of the desired product as a colorless oil.

Workup

customThe cooling agent was removed after 20 min
temperatureAfter 2 h the reaction mixture was cooled on an ice-bath before the addition of HCl (1M, 15 ml)
extractionThe mixture was extracted with dicloromethane
washthe organic phase was washed twice with water (15 ml)
dry with materialdried with NaSO4
customEvaporation
customgave 0.554 g, ˜100%

Sources & evidence

ORD record: ord-cb944b0f351045aaa8549de4cf744d73
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630509B2

Reaction notes

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