Diisobutylaluminumhydride → HCID 69198982, compound

HRID 898352Notes

Reaction equation

HRID 898352 reaction equation
C[O:2][C:3](=O)/[CH:4]=[C:5](\[C:8]1[CH:25]=[CH:24][C:11]2[C:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]([CH2:15][CH3:16])[O:14][C:10]=2[CH:9]=1)/[CH2:6][CH3:7].[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[CH2:17]([C:12]1[C:11]2[CH:24]=[CH:25][C:8](/[C:5](/[CH2:6][CH3:7])=[CH:4]\[CH2:3][OH:2])=[CH:9][C:10]=2[O:14][C:13]=1[CH2:15][CH3:16])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69200529HCID 69200529, compound

Product 1

HCID 69198982HCID 69198982, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-47.5 °C

Procedure

Z-3-(3-Benzyl-2-ethyl-benzofuran-6-yl)-pent-2-enoic acid methyl ester (6.0 g; 0.0173 mol) was dissolved in ether (200 mL) and the mixture was cooled to −45 to −50° C. Diisobutyl-aluminum hydride (100 mL of 1M solution in THF; 0.1 mol) was added dropwise. The mixture was stirred at −45 to −50° C. for 1 hour then at room temperature for 18 hours. The mixture was poured over a mixture of ice/2N HCl solution and extracted with ethyl acetate and ether, washed with 2N HCl and water, dried over anhydrous magnesium sulfate and solvent evaporated. The residue was purified by flash chromatography on silica gel using 4% ethyl acetate in Hexane as an eluent. The title compound was obtained (4.7 g) as an oil. 1HNMR (400 MHz, DMSO-d6): δ 0.88 (t, 2H, J=7.25 Hz), 1.22 (t, 3H, J=7.47 Hz), 2.37 (q, 2H, J=7.47 Hz), 2.84 (q, 3H, J=7.47 Hz), 3.81 (d, 2H, J=6.59 Hz), 3.96 (s, 2H), 4.5 (brs, 1H), 5.56 (t, 1H, J=6.59 Hz), 6.93 (dd, 1H, J=7.9, 1.32 Hz), 7.18-7.2 (m, 1H), 7.22-7.26 (m, 5H), 7.31 (d, 1H, J=7.9 Hz).

Workup

  1. waitat room temperature for 18 hours
  2. extractionextracted with ethyl acetate and ether
  3. washwashed with 2N HCl and water
  4. dry with materialdried over anhydrous magnesium sulfate and solvent
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel using 4% ethyl acetate in Hexane as an eluent

Sources & evidence

ORD record
ord-bcab06e4771d44eebbe89421772893bc
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

Loading…