Iodoethane → HCID 89827725, compound

HRID 715113Notes

Reaction equation

HRID 715113 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](I)[CH3:23]>C1COCC1>[CH2:15]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][CH2:10][C:11]([O:13][CH2:22][CH3:23])([CH3:14])[CH3:12])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 79309201HCID 79309201, compound

Product 1

HCID 89827725HCID 89827725, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a 0° C. solution of 4-(dibenzylamino)-2-methylbutan-2-ol (13 g, 45.9 mmol) in THF (200 mL), under N2, portion wise with KH (30%, 6.7 g, 50.9 mmol), stir at 0° C. for 0.5 h, add ethyl iodide (8.5 g, 55 mmol) drop-wise and warm to 60° C. overnight. Cool to 0° C., quench with satd. NH4Cl and concentrate partially. Extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (1.7 g, 12%). 1H NMR (400 MHz, DMSO-d6): δ 7.36-7.21 (m, 10H), 3.52 (s, 4H), 3.13 (t, J=7.2 Hz, 2H), 2.40-2.36 (m, 2H), 1.68-1.64 (m, 2H), 0.99 (m, 6H), 0.83 (q, J=7.2 Hz, 3H).

Workup

  1. temperaturewarm to 60° C. overnight
  2. temperatureCool to 0° C.
  3. customquench with satd
  4. concentrationNH4Cl and concentrate partially
  5. extractionExtract with EtOAc (3×)
  6. washwash the combined organics with brine
  7. dry with materialdry over Na2SO4
  8. concentrationconcentrate
  9. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-0ee325f6fd1441bba68b53521b336eba
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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