Triethylamine → [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

HRID 906437

반응식

HRID 906437 반응식
[Si:1]([O:8][CH2:9][C:10]1([CH2:13][OH:14])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.O>[CH3:22][S:23]([O:14][CH2:13][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:11][CH2:12]1)(=[O:25])=[O:24]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

생성물 1

HCID 59000927[1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol (Example 34c, 5.37 g) dissolved in DCM (20 mL) was treated with triethylamine (6.92 mL) at 0° C. before adding methanesulfonyl chloride (2.321 mL) under nitrogen. The resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with water (100 mL), and extracted with DCM (250 mL). The organics were dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography, elution 50% isohexane in diethyl ether). Pure fractions were evaporated to dryness to afford the subtitle compound (5.37 g) as an oil.

후처리

  1. extractionextracted with DCM (250 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified
  6. wash(SiO2 chromatography, elution 50% isohexane in diethyl ether)
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-2be7449450db4b7bb51f95b6aae5ad43
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012980B2

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