Water → 1-(Hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 132999Notes

Reaction equation

HRID 132999 reaction equation
[I:1][C:2]1[C:7]2[C:8](=[O:21])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17](OC)=[O:18])[C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1>[OH:18][CH2:17][C:13]1[C:10]2[CH:11]=[CH:12][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([I:1])[C:7]=3[CH:8]([OH:21])[C:9]=2[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 58646834Methyl 6-iodo-5-oxo-5H-dibenzo[a,d]cycloheptene-1-carboxylate2×

Product 1

HCID 586468371-(Hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg of the mixture of methyl 6-iodo-5-oxo-5H-dibenzo[a,d]cycloheptene-1-carboxylate and its 4-iodo form prepared in Example 6-d was dissolved in 5 ml of dry tetrahydrofuran, and 0.75 ml of a 1M solution of diisobutyl aluminium hydride in toluene was added at room temperature. To the reaction mixture was added with small amounts of water and ethyl acetate, followed by stirring at room temperature for 30 minutes. Then, the reaction mixture was filtered through Celite, washed with ethyl acetate, and the solvent was removed, to give 40 mg of a mixture of the title compound with its 4-iodo form as a colorless powder.

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-50c5691165a9496abce6efe3cd922400
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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