Acetic Acid → HCID 10759690, compound

HRID 411929Notes

Reaction equation

HRID 411929 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)([O-:3])=[O:2].[BH4-].[Na+].C(O)(=O)C.O>C1COCC1.CO>[N+:1]([CH2:4][CH2:5][C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 10712152HCID 10712152, compound

Product 1

HCID 10759690HCID 10759690, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Following the procedure for a β-unsubstituted pyrrole (Strachan, J. P. et al., J. Org. Chem. 2000, 65, 3160-3172), a sample of 18 (1.36 g, 4.00 mmol) was dissolved in anhydrous THF/MeOH (40 mL, 9:1) under argon at 0° C. NaBH4 (605 mg, 16.00 mmol) was added in portions and stirring was continued for 1 h at 0° C. Then the mixture was stirred for 2 h at room temperature. The reaction mixture was neutralized with acetic acid (pH=7), then water (50 mL) was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried (Na2SO4), concentrated, and purified by passage through a short column [silica, hexanes/ethyl acetate (3:1)] to give a pale white solid (1.2 g, 88%): mp 88-89° C.; 1H NMR δ 3.41 (t, J=6.6 Hz, 2H), 4.52 (t, J=6.6 Hz, 2H), 6.26 (s, 1H), 6.74 (s, 1H), 7.07 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.1 Hz, 2H), 8.33 (br, 1H); 13C NMR δ24.0, 75.0, 91.1, 109.3, 117.8, 122.1, 122.2, 129.8, 135.7, 137.7; FAB-MS obsd 341.9877, calcd 341.9865; Anal. Calcd for Cl2H11IN2O2: C, 42.1; H, 3.2; N, 8.2. Found: C, 42.3; H, 3.3; N, 8.1.

Workup

  1. stirringThen the mixture was stirred for 2 h at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by passage through a short column [silica, hexanes/ethyl acetate (3:1)]

Sources & evidence

ORD record
ord-95ce5d02b066424ba28dc86d88d66c43
Source dataset
uspto-grants-2003_05
Patent number
US06559374B2

Reaction notes

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