Diethylamine → HCID 11142490, compound

HRID 1404685Notes

Reaction equation

HRID 1404685 reaction equation
C(NCC)C.C([Li])CCC.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14].[O:25]1[CH2:29]C[CH2:27][CH2:26]1>>[CH2:11]([Sn:15]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[C:27]#[C:26][O:25][CH3:29])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 11142490HCID 11142490, compoundYield 78%

Conditions

Temperature
23 °C

Procedure

To a solution of freshly distilled diethylamine (9.6 mL, 92 mmol, 3.9 equiv) in tetrahydrofuran (300 mL) at 0° C. was added n-butyllithium (2.5 M in hexanes, 32 mL, 80 mmol 3.4 equiv). After stirring for 10 min, 1,1-dimethoxy-2-chloro-acetaldehyde (4.0 mL, 26 mmol, 1.1 equiv) was added dropwise to the reaction mixture. The reaction was stirred for 2 hours at 0° C. Tributyltin chloride (6.2 mL, 24 mmol, 1.0 equiv) was then added to the reaction mixture. The reaction was warmed to 23° C. over 1 hour and stirred for 8 hours. The volatiles were removed in vacuo and the reaction mixture was re-suspended in hexane (30 mL) and filtered through a glass frit under an argon atmosphere. The solution was then re-concentrated by rotary evaporation and distilled by Kugelrohr to yield 6.4 g (78%) of 10 as a colorless oil.

Workup

  1. stirringThe reaction was stirred for 2 hours at 0° C
  2. stirringstirred for 8 hours
  3. customThe volatiles were removed in vacuo
  4. filtrationfiltered through a glass frit under an argon atmosphere
  5. concentrationThe solution was then re-concentrated by rotary evaporation
  6. distillationdistilled by Kugelrohr

Sources & evidence

ORD record
ord-e60e99a6154e4aa5bde825e1db26f7f6
Source dataset
uspto-grants-2014_12
Patent number
US08912347B2

Reaction notes

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