Nitrogen → 2-(5-Chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

HRID 1189425노트

반응식

HRID 1189425 반응식
N#N.[CH3:3][C:4]1([C:9]2[O:13][C:12]([CH2:14]O)=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.S([Cl:27])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:27][CH2:14][C:12]1[O:13][C:9]([C:4]2([CH3:3])[O:8][CH2:7][CH2:6][O:5]2)=[CH:10][CH:11]=1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66929165[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol

생성물 1

HCID 669289652-(5-Chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol (3.50 g, 19.00 mmol) in dry CH2Cl2 (35.0 mL) was treated at 0° C. with Et3N (3.44 mL, 22.80 mmol) followed by DMAP (232 mg, 1.90 mmol) and Ms-Cl (1.77 mL, 22.80 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (40 mL), extracted with CH2Cl2 (40 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced. Purification of the residue by FC (8:2:0.1 hept-EA-Et3N) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.35.

후처리

  1. customthe reaction mixture was quenched with water (40 mL)
  2. extractionextracted with CH2Cl2 (40 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed
  6. customPurification of the residue by FC (8:2:0.1 hept-EA-Et3N)

출처 및 근거

ORD 기록
ord-cbc8413340ef464db9f0c75fcde16885
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674111B2

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