Methanesulfonyl chloride → HCID 86650639, 화합물

HRID 1963943노트

반응식

HRID 1963943 반응식
[CH3:1][C:2]1([CH3:10])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4][CH2:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:6]1[CH2:5][O:4][CH2:3][C:2]([CH3:10])([CH3:1])[O:7]1)(=[O:14])=[O:13]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66937181(6,6-Dimethyl-1,4-dioxan-2-yl)methanol

생성물 1

HCID 86650639HCID 86650639, 화합물수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TEA (0.52 mL, 3.74 mmol) and (6,6-dimethyl-1,4-dioxan-2-yl)methanol (390 mg, 2.67 mmol) were dissolved in DCM (10 mL). Methanesulfonyl chloride (0.249 mL, 3.20 mmol) was slowly added at 0° C. After the addition was completed the solution was warmed to ambient temperature and stirred for 1 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous layer was extracted three times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1) to give the product as a colorless oil (584 mg, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 4.00-4.09 (3H, m), 3.74 (1H, dd, J= 11.2, 2.8 Hz), 3.42 (1H, d, J= 11.6 Hz), 3.16-3.23 (2H, m), 2.99 (3H, s), 1.27 (3H, s), 1.05 (3H, s).

후처리

  1. additionAfter the addition
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted three times with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1)

출처 및 근거

ORD 기록
ord-77afdf421cf244fd931e5da4650af7b0
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415381B2

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