Iodoethane → HCID 66562536, compound

HRID 1844707Notes

Reaction equation

HRID 1844707 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=3)=[CH:11][C:10]([S:27]([NH2:30])(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:43][CH3:44]>C1COCC1>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=[C:15]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:14]=3)=[CH:11][C:10]([S:27]([NH:30][CH2:43][CH3:44])(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 66554786HCID 66554786, compound

Product 1

HCID 66562536HCID 66562536, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 1 (500 mg, 1.10 mmol) in dry THF (20 mL) was added LiHMDS (1.0 mL, 1.0 mmol) at −10° C. under N2. After stirring for 30 min, iodoethane (312 mg, 2.0 mmol) was added. The solution was stirred for another 3 h at 35° C., then quenched with water and extracted with EA twice. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, concentrated and purified by CC (EA/PE=1/5) to give compound 2 (50 mg, 10%) as a solid. 1H-NMR (400 MHz, CDCl3) δ: 0.63-0.65 (m, 2H), 0.97-1.03 (m, 3H), 1.13-1.17 (m, 3H), 1.34 (s, 18H), 1.32-1.35 (m, 3H), 1.50-1.55 (m, 3H), 2.52 (s, 3H), 3.04-3.07 (m, 2H), 3.72 (d, J=6.8 Hz, 2H), 4.12 (m, 1H), 6.41 (s, 1H), 7.15 (s, 2H), 7.40 (s, 1H). MS Calcd.: 472; MS Found: 473 (M+1).

Workup

  1. stirringThe solution was stirred for another 3 h at 35° C.
  2. customquenched with water
  3. extractionextracted with EA twice
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (EA/PE=1/5)

Sources & evidence

ORD record
ord-c498be4b0db94389a3464a23a1c852bf
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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