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Hydrochloric Acid → 2,6,13,17-Tetramethyloctadecane-9,10-dione

HRID 1176160
Notes
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Reaction equation

HRID 1176160 reaction equation
CN1CCN(C)[C:4](=[O:9])[C:3]1=[O:10].[CH3:11][CH:12]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:14][Li].[CH3:22][CH:23]([CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:24][CH2:25]Br.[Li].Cl>CCOCC>[CH3:31][CH:30]([CH2:29][CH2:28][CH2:27][CH:23]([CH3:22])[CH2:24][CH2:25][C:4](=[O:9])[C:3](=[O:10])[CH2:14][CH2:13][CH:12]([CH3:11])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1379141-Bromo-3,7-dimethyloctaneHCID 3229831,4-Dimethylpiperazine-2,3-dioneHCID 3028194LithiumHCID 178506868HCID 178506868, compound

Product 1

HCID 874415822,6,13,17-Tetramethyloctadecane-9,10-dione

Reagents, catalysts & solvents

1
HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 1,4-dimethylpiperazine-2,3-dione (2.08 g, 1.46×10−2 mol) in 50 ml of dry Et2O was added 3,7-dimethyloctyl lithium (0.45M solution in Et2O, 65 ml, 2.9×10−2 mol, freshly prepared from 3,7-dimethyloctyl bromide and lithium) by a syringe. After 40 min of stirring at room temperature under N2, the solution was hydrolyzed with 100 ml of 10% HCl and extracted with CHCl3. The combined organic layers were washed with saturated aqueous NaHCO3 and dried over Na2SO4. The product was chromatographed on silica gel with 3:1 hexane:CHCl3 as the eluent. Yield=4.446 g (91% based on 65 ml of 0.45M 3,7-dimethyloctyl lithium in Et2O). 1H NMR (250 MHz, CDCl3): δ 2.69-2.78 (m, 4H, —CH2CO), 1.06-1.65 (m, 20H, (CH3)2CHCH2CH2CH2CH(CH3)CH2CH2CO), 0.87 (d, 6H, J=9.0 Hz, —CH3), 0.86 (d, 12H, J=9.5 Hz, —CH3). CI MS m/z: 338.3175 (M+) (calcd 338.318).

Workup

  1. extractionextracted with CHCl3
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. customThe product was chromatographed on silica gel with 3:1 hexane

Sources & evidence

ORD record
ord-47f814aca5f941d7bff548479971058c
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842758B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes