Diisopropylamine → HCID 54542911, compound

HRID 1720199Notes

Reaction equation

HRID 1720199 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl-].[CH3:14][O:15][CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:37]([CH2:44][CH:45]([CH3:52])[CH2:46][CH:47]([CH3:51])[CH2:48][CH2:49][CH3:50])[CH2:38][CH:39]([CH3:43])[C:40]([OH:42])=[O:41]>C1COCC1.CCCCCC>[CH3:52][CH:45]([CH2:46][CH:47]([CH3:51])[CH2:48][CH2:49][CH3:50])[CH2:44][C:37](=[CH:14][O:15][CH3:16])[CH2:38][CH:39]([CH3:43])[C:40]([OH:42])=[O:41]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 15332458HCID 15332458, compoundHCID 178418339Butyllithium

Product 1

HCID 54542911HCID 54542911, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisopropylamine (5.40 ml, 38.53 mmol) in 50 ml dry THF at -78° C. was mixed with 15.41 ml (38.53 mmol) of a 2.5M solution of n-butyllithium in hexane with stirring. After 15 minutes, (methoxymethyl)triphenyl-phosphonium chloride (13.87 g, 39.25 mmol, 97% purity) was slowly added. The temperature of the solution was raised to 0° C. and stirred for another 15 minutes. A solution of 4-oxo-2,6,8-trimethylundecanoic acid (10) (1.90 g, 7.85 mmol) in 20 ml of THF was then added to the reaction mixture and this mixture was stirred at room temperature for 11 hours.

Workup

  1. stirringstirred for another 15 minutes
  2. stirringthis mixture was stirred at room temperature for 11 hours

Sources & evidence

ORD record
ord-129434189f334c62a95c1592876c30f2
Source dataset
uspto-grants-1996_04
Patent number
US05505951

Reaction notes

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