Triethylamine → Nonyl methanesulfonate

HRID 15491

반응식

HRID 15491 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 15669353Nonyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-0b138ef870c548c0be2ea53537103d90
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732617B2

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