Ethyl Acetate → HCID 63630296, compound

HRID 2364536Notes

Reaction equation

HRID 2364536 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][CH2:6][NH:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].CCOC(C)=O.OS([O-])(=O)=O.[Na+]>C1COCC1>[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 516919Sodium BisulfateHCID 2733832Lithium Hexamethyldisilazide2×HCID 86612800HCID 86612800, compound

Product 1

HCID 63630296HCID 63630296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[3,3-bis(ethyloxy)propyl]-5-chloropentanamide (10 g, 38 mmol) in THF (400 mL) was treated with lithium hexamethyl disilazide (LiHMDS, 1.0 M in THF) (40 mL, 40 mmol) at ambient temperature. After stirring for 15 min., an additional 10 mL of LiHMDS was added and the reaction was stirred an additional 30 min. After TLC (EtOAc) showed the absence of starting material, the reaction was poured into a sep. funnel containing EtOAc (500 mL) and 1N NaHSO4 (500 mL). Back extracted the aqueous with EtOAc then combined the organics, washed them with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide the product as a clear viscous oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.02 Hz, 6 H), 1.63-1.74 (m, 6 H), 2.17 (t, J=6.11 Hz, 2 H), 3.20-3.28 (m, 4 H), 3.42 (dq, J=9.55, 7.07 Hz, 2 H), 3.56 (dq, J=9.55, 7.07 Hz, 2 H), 4.47 (t, J=5.62 Hz, 1 H).

Workup

  1. stirringthe reaction was stirred an additional 30 min
  2. additionthe reaction was poured into a sep
  3. extractionBack extracted the aqueous with EtOAc
  4. washwashed them with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ec5061fb3b74fb2bb4e3ad7aad7cbd6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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