Diisobutylaluminum hydride → HCID 69583696, compound

HRID 860573Notes

Reaction equation

HRID 860573 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C:21](OCC)=[O:22])[CH:15]=[CH:14]3)[CH:5]=[C:6]2[O:10][CH2:9][O:8][C:7]=12.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([CH2:21][OH:22])[CH:15]=[CH:14]3)[CH:5]=[C:6]2[O:10][CH2:9][O:8][C:7]=12

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69583773HCID 69583773, compound

Product 1

HCID 69583696HCID 69583696, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 6-[3-bromo-4,5-methylenedioxyphenyl]-2-naphthoate (18.32 g, 45.90 mmol) in 308 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (92 mL, 1.5 M in toluene, 137.7 mmol) dropwise. After 1 hour the reaction mixture was quenched with ethyl acetate and the resulting mixture was allowed to warm to RT. The mixture was diluted with ethyl acetate and washed with 5% NH4Cl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated. The residue was passed through a short silica gel column (eluent: CH2Cl2) to give 16.40 g of 6-[3-bromo-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methyl alcohol (100%). 1H NMR (300 MHz; CDCl3): δ 4.85 (s, 2H), 6.01 (s, 2H), 6.88 (s, 1H), 7.13 (s, 1H), 7.47 (dd, J1=4.0 Hz, J2=1.8 Hz, 1H), 7.50 (dd, J1=4.0 Hz, J2=1.8 Hz, 1H), 7.76–7.85 (m, 4H).

Workup

  1. customAfter 1 hour the reaction mixture was quenched with ethyl acetate
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with 5% NH4Cl, water and brine
  4. dry with materialThe organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-57f53a5a3cfa42f28a068a2be14c3c8e
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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