Diisobutylaluminumhydride → (E)-5-(3,5-dichloro-phenyl)-pent-2-en-4-yn-1-ol

HRID 1270065Notes

Reaction equation

HRID 1270065 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)/[CH:15]=[CH:16]/[C:17]#[C:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=1)C>Cl>[Cl:25][C:23]1[CH:24]=[C:19]([C:18]#[C:17]/[CH:16]=[CH:15]/[CH2:14][OH:13])[CH:20]=[C:21]([Cl:26])[CH:22]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86583979(E)-5-(3,5-dichlorophenyl)-pent-2-en-4-ynoic acid ethyl ester

Product 1

HCID 18522394(E)-5-(3,5-dichloro-phenyl)-pent-2-en-4-yn-1-ol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisobutylaluminium hydride (1.0 M solution in toluene, 20 mL, 20 mmol) at −78° C. was slowly added (E)-5-(3,5-dichloro-phenyl)-pent-2-en-4-ynoic acid ethyl ester (1.1 g, 4.08 mmol). The reaction mixture was stirred for 2 h at −78° C., where after the reaction mixture was poured into hydrocloride acid (6N, 50 mL) and extracted with diethyl ether (3×40 mL) The combined and dried organic phases were evaporated to give crude (E)-5-(3,5-dichloro-phenyl)-pent-2-en-4-yn-1-ol in 750 mg yield.

Workup

  1. customat −78° C.
  2. extractionextracted with diethyl ether (3×40 mL) The
  3. customdried organic phases were evaporated

Sources & evidence

ORD record
ord-2a220148f4174501bcf080f112cecdd9
Source dataset
uspto-grants-2007_04
Patent number
US07202213B2

Reaction notes

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