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

HRID 1189425ノート

反応式

HRID 1189425 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cbc8413340ef464db9f0c75fcde16885
出典データセット
uspto-grants-2014_03
特許番号
US08674111B2

反応ノート

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