Triethylamine → Nonyl methanesulfonate

HRID 15491

Reaction equation

HRID 15491 reaction equation
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19].CC1C=CN=C(N)C=1C>C(Cl)Cl>[CH3:21][S:18]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 89141-NonanolHCID 31297Methanesulfonyl chlorideHCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 15669353Nonyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.08 mmol) of (R)-9-(6-tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonanol was dissolved in dry DCM (10 ml) under argon atmosphere, followed by the addition of triethylamine (224 ul), MsCl (mesylchloride) (125 ul) and a catalytic amount of DMAP (dimethyl amino pyridine) at 0° C. After 15 minutes the cooling bath was removed and the reaction stirred at room temperature for 1.5 hours. TLC monitoring showed complete conversion in 100% DCM as mobile phase. Extraction with water and DCM afforded crude product that was obtained following evaporation of the solvent under reduced pressure. Column chromatography on silica (100% DCM) gave pure (R)-9-(6-tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonyl methanesulfonate in high yields (following high vacuum). (90%, 526 mg, 0.97 mmol)

Workup

  1. customat 0° C
  2. customAfter 15 minutes the cooling bath was removed
  3. extractionExtraction with water and DCM
  4. customafforded crude product that
  5. customwas obtained
  6. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0b138ef870c548c0be2ea53537103d90
Source dataset
uspto-grants-2010_06
Patent number
US07732617B2

Linked notes

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