Acetic Anhydride → (5-Hydroxy-6-iodo-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

HRID 133000Notes

Reaction equation

HRID 133000 reaction equation
[OH:1][CH2:2][C:3]1[C:13]2[CH:12]=[CH:11][C:10]3[CH:14]=[CH:15][CH:16]=[C:17]([I:18])[C:9]=3[CH:8]([OH:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O1CCCC1>[C:20]([O:1][CH2:2][C:3]1[C:13]2[CH:12]=[CH:11][C:10]3[CH:14]=[CH:15][CH:16]=[C:17]([I:18])[C:9]=3[CH:8]([OH:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 586468371-(Hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol2×

Product 1

HCID 58646838(5-Hydroxy-6-iodo-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

310 mg of the mixture of 1-(hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol with its 4-iodo form prepared in Example 6-e was dissolved in 15 ml of methylene chloride, and 100 mg of 4-(dimethylamino)pyridine and 0.8 ml of 1M solution of acetic anhydride in tetrahydrofuran were added under ice-cooling, followed by stirring at room temperature for 2 hours. The solvent was evaporated, and the residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=3:17), to give 230 mg of a mixture of the title compound with its 4-iodo form as a colorless powder.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. customthe residue was purified
  4. customseparated by silica gel column chromatography (ethyl acetate:hexane=3:17)

Sources & evidence

ORD record
ord-fadeac3b4c3b466aa997f457709be1d0
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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