Toluene → HCID 68933976, compound

HRID 2218775Notes

Reaction equation

HRID 2218775 reaction equation
C[O:2][C:3](=O)[CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[C:5](=[CH:4][CH2:3][OH:2])[C:6]3[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=3[CH2:8][CH2:9][C:10]=2[CH:15]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 68935575HCID 68935575, compound

Product 1

HCID 68933976HCID 68933976, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

Dissolve (2-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)acetic acid methyl ester (1 equivalent) in a suitable dry solvent and cool to 0° C. under a dry atmosphere. Add 1M diisobutylaluminum hydride solution in toluene (3 equivalents) dropwise and stir the mixture for one hour. Quench with aqueous citric acid solution and partition between water and ethyl acetate. Dry and evaporate the organic layer to obtain the title compound in 87% yield.

Workup

  1. customQuench with aqueous citric acid solution
  2. custompartition between water and ethyl acetate
  3. customDry
  4. customevaporate the organic layer

Sources & evidence

ORD record
ord-0fdfe708e6c44b1a859c9597f420c55a
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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