Triethylamine → 2-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate

HRID 1350121

반응식

HRID 1350121 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:20])=[O:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 177509442-(Oxan-4-yl)ethan-1-ol

생성물 1

HCID 222730832-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate수율 77.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of 2-(4-oxanyl)ethanol (9.63 g, 74.0 mmol) in dry dichloromethane (350 mL) was added distilled triethylamine (20.62 mL, 96.2 mmol) at 0° C., followed by drop-wise addition of methanesulfonyl chloride (7.44 mL, 96.2 mmol) over 15 min. The reaction was stirred for 16 h under N2 and slowly allowed to come to ambient temperature. The reaction was washed with saturated NaHCO3 (100 mL) and the aqueous phase was extracted with dichloromethane (1×50 mL). The combined organic extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to yield 11.9 g of a colorless oil (77.0% yield).

후처리

  1. customto come to ambient temperature
  2. washThe reaction was washed with saturated NaHCO3 (100 mL)
  3. extractionthe aqueous phase was extracted with dichloromethane (1×50 mL)
  4. dry with materialThe combined organic extracts were dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-b2772805d058453d89e0f64d57eedb50
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214686B2

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