Diisobutylaluminumhydride → (1-benzyl-2-chloro-5-phenyl-1H-pyrrol-3-yl)methanol

HRID 505822Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:19](OC)=[O:20])=[C:9]1[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][C:10]([CH2:19][OH:20])=[C:9]1[Cl:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution (0.24 M) of methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylate in DCM at −78° C. was treated with diisobutylaluminium hydride (1 M solution in DCM, 2.5 eq.). The resulting solution was stirred at −78° C. for 2 h then it was warmed to 0° C. and quenched with MeOH. The Rochelle solution (10% wt sodium and potassium tartrate) was added and the mixture was stirred at RT for 1 h (until two phases came out). The mixture was extracted with DCM and the combined organic phase was treated with brine and dried. Evaporation of the solvent afforded the title compound (90%) as an oil.

Workup

temperatureit was warmed to 0° C.
customquenched with MeOH
additionThe Rochelle solution (10% wt sodium and potassium tartrate) was added
stirringthe mixture was stirred at RT for 1 h (until two phases came out)
extractionThe mixture was extracted with DCM
additionthe combined organic phase was treated with brine
customdried
customEvaporation of the solvent

Sources & evidence

ORD record: ord-16dd888a92e04b4d9379ffdca2aa657b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781431B2

Reaction notes

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