Diisobutylaluminumhydride → 2-Allyl-2-(4-bromo-phenyl)-pent-4-en-1-ol

HRID 658290Notes

Reaction equation

HRID 658290 reaction equation
C([O:3][C:4](=O)[C:5]([CH2:16][CH:17]=[CH2:18])([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[CH2:6][CH:7]=[CH2:8])C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH2:6]([C:5]([C:9]1[CH:10]=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=1)([CH2:16][CH:17]=[CH2:18])[CH2:4][OH:3])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 674861212-Allyl-2-(4-bromo-phenyl)-pent-4-enoic acid ethyl ester

Product 1

HCID 674858602-Allyl-2-(4-bromo-phenyl)-pent-4-en-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude 2-allyl-2-(4-bromo-phenyl)-pent-4-enoic acid ethyl ester (2.64 g) in CH2Cl2 (40 mL) at 0° C. is treated with diisobutylaluminum hydride (1.0 M toluene, 17.5 mL) dropwise for 8 min, warmed to room temperature, and stirred for 45 min. The reaction mixture is cooled to 0° C., quenched with 1M tartaric acid (25 mL), and stirred overnight. The organic layer is separated and the aqueous layer is extracted with CH2Cl2 (3×25 mL). The combined organic extracts are dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% EtOAc to 50% EtOAc to provide 1.319 g (56%-2 steps) of the title compound as a light yellow oil. 1H NMR (CDCl3): δ 7.47-7.43 (m, 2H), 7.23-7.19 (m, 2H), 5.59 (ddt, J=17.1, 10.2, 6.7 Hz, 2H), 5.09-5.01 (m, 4H), 3.76 (d, J=6.8 Hz, 2H), 2.48 (dd, J=14.1, 6.8 Hz), 2.42 (dd, J=13.6, 7.2 Hz, 2H), 1.29 (t, J=6.1 Hz).

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. customquenched with 1M tartaric acid (25 mL)
  3. stirringstirred overnight
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted with CH2Cl2 (3×25 mL)
  6. dry with materialThe combined organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluted with hexanes using a gradient of 0% EtOAc to 50% EtOAc

Sources & evidence

ORD record
ord-c7e2bc8baf6241cc9c7b0b1eafd4ed6b
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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