Tetrahydrofuran → HCID 178444053, compound

HRID 923586Notes

Reaction equation

HRID 923586 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#N)=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C1C[O:40]CC1>O.CC(=O)OCC>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([CH:23]=[O:40])=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 178444049HCID 178444049, compound

Product 1

HCID 178444053HCID 178444053, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazole-5-carbonitrile INT-46 (1.22 g, 3.51 mmol) in THF (20 mL) at 0° C. was added diisobutylaluminum hydride (12.3 mL, 12.3 mmol, 1 M in toluene). After 2 h the reaction mixture was poured onto Rochelle's salt (7.91 g, 28.0 mmol) in water (100 mL) and EA (50 mL) and stirred for 1 h. The layers were split and the aqueous layer was further extracted with EA (2×30 mL). The combined organics were washed with brine (20 mL) dried over MgSO4 and evaporated. The crude material was purified by chromatography (EA/isohexanes) to afford 571 mg (46%) of 2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazole-5-carbaldehyde INT-47 as a brown oil. LCMS-ESI (m/z) calculated for C22H26N2O2: 350; found 351 [M+H]−, tR=2.34 min (Method 5).

Workup

  1. customThe layers were split
  2. extractionthe aqueous layer was further extracted with EA (2×30 mL)
  3. washThe combined organics were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude material was purified by chromatography (EA/isohexanes)

Sources & evidence

ORD record
ord-45a0cb3f93ca431b95cbaba6fd2ed787
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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