Trimethylaluminum → HCID 86693330, compound

HRID 575299Notes

Reaction equation

HRID 575299 reaction equation
[I:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][C:8](=[O:19])[C:9]3[N:10]([N:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=3)[C:4]=2[CH:3]=1.[CH3:22][Al](C)C>ClCCl>[OH:19][C:8]1([CH3:22])[CH2:7][O:6][C:5]2[CH:20]=[CH:21][C:2]([I:1])=[CH:3][C:4]=2[N:10]2[N:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=[C:9]12

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 86693331HCID 86693331, compound

Product 1

HCID 86693330HCID 86693330, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution ethyl 9-iodo-4-oxo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (3 g, 7.53 mmol, 1.00 equiv) in dichloromethane (50 mL) was added trimethylalumane (2.0M in toluene) (4.5 mL, 1.20 equiv) at −10° C. After being stirred for 2 hours at −10° C. the resulting solution was diluted with 20 mL of dichloromethane, washed with saturated ammonia chloride, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:2) to give 2.4 g (77%) of the titled compound as a light yellow solid; LC-MS (ES, m/z): 415 [M+H]+.

Workup

  1. washwashed with saturated ammonia chloride
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:2)

Sources & evidence

ORD record
ord-d1dd78070e2c4da1a1d59568d1d88fae
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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