Triethylamine → Phytanyl Mesylate

HRID 883568Notes

Reaction equation

HRID 883568 reaction equation
[CH2:1]([OH:21])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4].C(N(CC)CC)C.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>C(Cl)Cl>[S:29]([O:21][CH2:1][CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4])(=[O:31])(=[O:30])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 102459Dihydrophytol

Product 1

HCID 60047967Phytanyl Mesylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

Phytanol (20.0 g, 66.7 mmol), triethylamine (18.6 mL, 133 mmol) and a stir bar were added to a 1000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (250 mL) was added, and the mixture cooled to −15° C. (Ice and NaCl). Mesyl Chloride (10.4 mL, 133 mmol) was added slowly via syringe over a 30 minute period, and the reaction stirred at −15° C. for a further 1.5 hours. At this point TLC showed that the starting material had been used up. The solution was diluted with DCM (250 mL) and washed with saturated NaHCO3 (2×200 mL). The organic phase was then dried (MgSO4), filtered and concentrated (rotovap). The crude product was purified by column chromatography. Yield 21.5 g, 85.7%.

Workup

  1. customThe flask was sealed
  2. customflushed with nitrogen
  3. additionAnhydrous DCM (250 mL) was added
  4. washwashed with saturated NaHCO3 (2×200 mL)
  5. dry with materialThe organic phase was then dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated (rotovap)
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-25b6a7be1fca4f58b852f5a82961f0f3
Source dataset
uspto-grants-2012_08
Patent number
US08236943B2

Reaction notes

Loading…