Myristyl bromide → HCID 21839216, compound

HRID 1738772Notes

Reaction equation

HRID 1738772 reaction equation
[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CC([O-])(C)C.[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CC(O)(C)C>[CH3:13][C:12]([O:11][C:1](=[O:10])[CH:2]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 68324Di-tert-butyl malonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21839216HCID 21839216, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of di-tert butyl malonate (10.80 g, 50 mmol) and t-BuOK (5.60 g, 50 mmol) was stirred (30 min, 75° C.) in t-BuOH (150 mL, dried over 4A sieves). To this was added a solution of 1-bromotetradecane (13.85 g, 50 mmol) and the reaction stirred at 75° C. overnight. Solvent was removed by rotary evaporation, giving a white semi-solid, which was partitioned between CH2Cl2 (100 mL) and saturated aqueous NaCl (2×300 mL), dried (MgSO4) and evaporated to a colorless oil (15.3 g). Purification by silica gel flash chromatography (100% hexane incremented to hexane:CH2Cl2 (70:30)) gave product (34) as a colorless oil (10.0 g, 48%). High resolution FAB MS:C25H49O4 (M+H); Theor. 413.3630855. Found 413.3627625.

Workup

  1. customSolvent was removed by rotary evaporation
  2. customgiving a white semi-solid, which
  3. customwas partitioned between CH2Cl2 (100 mL) and saturated aqueous NaCl (2×300 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a colorless oil (15.3 g)
  6. customPurification by silica gel flash chromatography (100% hexane incremented to hexane:CH2Cl2 (70:30))

Sources & evidence

ORD record
ord-a3f6551a1e27440ea7b5225626254205
Source dataset
uspto-grants-1999_10
Patent number
US05965524

Reaction notes

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