Triethylamine → 4-Ethynylbenzyl methanesulfonate

HRID 1929301

반응식

HRID 1929301 반응식
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[CH:2].C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>C(Cl)Cl>[CH3:21][S:18]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[CH:2])=[CH:4][CH:5]=1)(=[O:20])=[O:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11170993(4-Ethynylphenyl)methanol

생성물 1

HCID 594357734-Ethynylbenzyl methanesulfonate수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-ethynylbenzyl alcohol (5.0 g, 37.8 mmol) in CH2Cl2 (50 mL) and triethylamine (Et3N) (14.4 mL, 104.0 mmol) was added mesyl chloride (8.04 mL, 104.0 mmol) at 0° C. and the reaction was allowed to warm to room temperature. Stirring continued for 2 h under argon during which TLC revealed a quantitative conversion into a higher Rf product. Ice cold water was added into the reaction mixture and extracted with Et2O (200 ml). The organic layer was washed with 1N HCL (70 ml), H2O (100 ml), aqueous NaHCO3 (70 ml), and finally H2O (100 ml); and then dried over Na2SO4. Solvent was evaporated off and dried in vacuo to give 7.0 g of compound 3 as brownish oil which was used without further purification.

후처리

  1. additionIce cold water was added into the reaction mixture
  2. extractionextracted with Et2O (200 ml)
  3. washThe organic layer was washed with 1N HCL (70 ml), H2O (100 ml), aqueous NaHCO3 (70 ml), and finally H2O (100 ml)
  4. dry with materialand then dried over Na2SO4
  5. customSolvent was evaporated off
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-9b05b4722aaf48edbf4f4439c833e9fa
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188054B2

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