Toluene → HCID 58938005, compound

HRID 1182046Notes

Reaction equation

HRID 1182046 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:20]=1)#N.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.CC(O)=[O:39].O>C(Cl)Cl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:20]=1)=[O:39]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 21899381Acetic acid--water (1/1)HCID 58938010HCID 58938010, compound

Product 1

HCID 58938005HCID 58938005, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from step 3 (2.5 g, 9.5 mmol) in dry CH2Cl2 (320 mL), cooled at −78° C. and under N2 atmosphere, add DIBAL 10M in toluene (28.4 mmol). Allow the mixture to warm to room temperature and stir overnight. Cool the mixture to 0° C. and add AcOH/H2O. Stir at room temperature for 1 hour. Extract the aqueous layer with CH2Cl2 (×2). Combine the organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography (eluent: EtOAc/hexane 3/1) to obtain the title compound (1.75 g, 69%). 1H-NMR (MeOD, 300 MHz): 9.91 (s, 1H), 7.81-7.73 (m, 4H), 7.37-7.26 (m, 2H), 3.21 (m, 4). 13C-NMR (MeOD, 300 MHz): 193.2, 162.6, 160.3, 134.4, 133.8, 133.2, 131.9, 131.3, 130.6, 128.8, 123.3, 122.4, 32.9, 32.8.

Workup

  1. temperatureCool the mixture to 0° C.
  2. stirringStir at room temperature for 1 hour
  3. extractionExtract the aqueous layer with CH2Cl2 (×2)
  4. dry with materialCombine the organic layers and dry over Na2SO4
  5. custompurify by flash chromatography (eluent: EtOAc/hexane 3/1)

Sources & evidence

ORD record
ord-0b0448189ee948d387b960da54c328fe
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

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