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

HRID 505822
Notes
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Reaction equation

HRID 505822 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68468834methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 68472482(1-benzyl-2-chloro-5-phenyl-1H-pyrrol-3-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. temperatureit was warmed to 0° C.
  2. customquenched with MeOH
  3. additionThe Rochelle solution (10% wt sodium and potassium tartrate) was added
  4. stirringthe mixture was stirred at RT for 1 h (until two phases came out)
  5. extractionThe mixture was extracted with DCM
  6. additionthe combined organic phase was treated with brine
  7. customdried
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes