Sodium Chloride → HCID 10518344, compound

HRID 1075480Notes

Reaction equation

HRID 1075480 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]([O:16][C@@H:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][C:19](OC)=[O:20])([CH3:15])[CH3:14].[Cl-].[Na+]>C1(C)C=CC=CC=1.CO>[CH3:11][O:12][C:13]([O:16][C@@H:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][CH:19]=[O:20])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 10592560HCID 10592560, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10518344HCID 10518344, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

Diisobutylaluminium hydride (10.7 mL, 60 mmol) dissolved in toluene (30 mL) was precooled to -80° C. and added during 1 h at a temperature of -80° C. to a solution of the crude methyl (S)-3-(2-methoxyprop-2-oxy)tetradecanoate (IX, 13.20 g, 40 mmol) in toluene (100 mL), obtained according to the foregoing described procedure. After complete addition the mixture was stirred for an additional 30 min, diluted with methanol (10 mL), and allowed to warm up to room temperature. A saturated aqueous solution of sodium chloride was added and the precipitate removed by filtration over a pad of fine sand. The filter cake was washed with ethyl acetate (5×15 mL). Filtrate and washings were combined. The aqueous phase was separated and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with water (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The residual colorless oil (13.7 g, containing still traces of toluene) was used in the next step without further purification. [α]25D +4.89 (c=0.5 in hexane); 1H NMR (DMSO-D6) δ 0.86 (t, J=7 Hz, 3H), 1.24-1.69 (m, 26H), 3.08 (s, 3H), 4.17-4.21 (m, 1H), 9.67 (t, J=2 Hz, 1H), 13C NMR (DMSO-D6) δ 13.85, 22.05, 24.49, 24.87, 24.96, 28.68, 28.94, 28.97, 29.00, 29.04, 31.28, 35.56, 48.50, 48.93, 66.25, 100.48, 202.80. Anal. Calcd for C18H36O4 : C, 71.95; H, 12.08. Found: C, 72.05; H, 12.28.

Workup

  1. customwas precooled to -80° C.
  2. customobtained
  3. additionAfter complete addition the mixture
  4. customthe precipitate removed by filtration over a pad of fine sand
  5. washThe filter cake was washed with ethyl acetate (5×15 mL)
  6. customThe aqueous phase was separated
  7. extractionextracted with ethyl acetate (3×20 mL)
  8. washThe combined organic phases were washed with water (10 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated under reduced pressure
  11. additionThe residual colorless oil (13.7 g, containing still
  12. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-84e185c34dec45bfa3a9795101ecca76
Source dataset
uspto-grants-1999_05
Patent number
US05902886

Reaction notes

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