Dichloromethane → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 78704

반응식

HRID 78704 반응식
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(Cl)Cl>O.C1COCC1>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH3:3])(=[O:22])=[O:21])=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8178Triethylene glycol monomethyl etherHCID 14798Sodium Hydroxide

생성물 1

HCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate수율 83%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of NaOH (1.69 g, 42.2 mmol) in H2O (11 mL) was added a solution of triethylene glycol monomethyl ether (5.00 mL, 31.9 mmol) in THF (11 mL) under nitrogen, while the temperature was maintained below 5° C. by cooling with an ice-salt bath. At the same temperature, a solution of p-toluenesulfonyl chloride (6.08 g, 31.9 mmol) in THF (13 mL) was added dropwise over 1 h. The reaction mixture was poured into water and DCM was added. The layers were separated, and the aqueous layer was extracted with DCM (three times). The combined organic layers were washed with water (twice) and brine (twice), dried over anhydrous MgSO4, filtered off and evaporated to dryness to give 16 (8.43 g, 83%): 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=8.3 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 4.16 (t, 2H), 3.50-3.70 (m, 10H), 3.32 (s, 3H), 2.40 (s, 3H).

후처리

  1. temperaturewhile the temperature was maintained below 5° C.
  2. temperatureby cooling with an ice-salt bath
  3. additionwas added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (three times)
  6. washThe combined organic layers were washed with water (twice) and brine (twice),
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered off
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-fccf92e18e414a3081ce368e79631bfb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841460B2

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